Water-soluble azo compound or salt thereof, ink and recording medium

ABSTRACT

A compound represented by formula (1) or a salt thereof, and an ink including the same. In formula (1), each Q independently represents a halogen atom; R 11  and R 12  independently represent an alkyl group substituted by an ionic hydrophilic group; and A 1  represents a C1-C3 alkoxy-substituted alkylamino group

This application is the U.S. National Phase under 35 U.S.C. § 371 of International Application PCT/JP2017/038038, filed Oct. 20, 2017, designating the U.S., and published in Japanese as WO 2018/079442 on May 3, 2018 which claims priority to Japanese Patent Application Nos. 2016-213232, 2016-213233, 2016-213234, and 2016-213238, all filed Oct. 31, 2016; and to Japanese Patent Application Nos. 2017-023615, 2017-023616, 2017-023617, 2017-023618, 2017-023619, and 2017-023620, all filed Feb. 10, 2017, the entire contents of which are incorporated herein by reference.

TECHNICAL FIELD

The present invention relates to a water-soluble azo compound or a salt thereof, an ink containing the water-soluble azo compound or a salt thereof, a method of ink-jet recording with the ink, an ink-jet printer having a container for the ink, and a recording medium on which the water-soluble azo compound or a salt thereof or the ink is attached.

BACKGROUND ART

Various ink discharging systems have been developed for a method of recording with an ink-jet printer, which is one of representative methods of various color recording methods. These systems all involve generating a droplet of ink, which is then allowed to attach to various recording media (paper, film, textile and the like), thereby performing recording. This method is quiet since a recording head does not make direct contact with a recording medium, generating no sound. Further, these systems, which can easily be downsized, accelerated, and adapted to full-color, have become increasingly popular in recent years, and significant and continuous growth is expected.

Conventionally, coloring matters for use in various recording inks that find their uses in fountain pens felt-tip pens, ink-jet recording and the like may be classified broadly into two groups: water-soluble and water-insoluble coloring matters. Water-soluble coloring matters include direct dyes, acid dyes, reactive dyes and the like. Water-insoluble coloring matters include pigments, disperse dyes, solvent dyes and the like. Among these coloring matters, dyes are thought to have excellent color saturation and the like as compared with pigments, leading to high quality recorded images. However, the robustness of recorded images such as light resistance may be inferior as compared with that of pigments.

The term “light resistance” as used herein refers to being resistant to a phenomenon where a coloring matter attached on a recorded image will undergo degradation due to exposure to various types of light such as sunlight and light from fluorescent lamps, resulting in discoloration of the recorded image. As one of the features of ink-jet recording, mentioned is the ability of producing photo-quality recorded images. As one of the methods of obtaining a photo-quality recorded image, mentioned is the use of a recording medium having an ink receiving layer. Such an ink receiving layer generally includes a porous white inorganic substance in order to achieve rapid drying of an ink, and obtain a high-quality image with less color blurring. Nonetheless, a significant light-induced discoloring phenomenon may be observed in such a recording medium. For this reason, improving light resistance of recorded images is considered as one of the most important technical issues in the art of ink-jet recording.

Patent Documents 1 to 3 disclose C.I. Direct Yellow 132 as a known yellow coloring matter for ink-jet with excellent water solubility and vividness. Moreover, Patent Document 4 discloses a yellow coloring matter for ink-jet that is excellent in terms of various aspects of robustness.

-   Patent Document 1: Japanese Unexamined Patent Application,     Publication No. H11-70729 -   Patent Document 2: Japanese Patent No. 3346755 -   Patent Document 3: Japanese Patent No. 4100880 -   Patent Document 4: PCT International Publication No. WO2011/122427

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

An object of the present invention is to provide a water-soluble azo compound capable of producing a recorded image with excellent light resistance, and a yellow ink containing the above compound for use in various types of recording, in particular an ink-jet recording purpose.

Means for Solving the Problems

After conducting extensive studies to solve the above described problems, the present inventors have found that a specific water-soluble azo compound represented by the following formula and an ink containing the above compound can solve the above problems, leading to the completion of the present invention.

That is, the present invention relates to the following 1) to 30).

1) A compound represented by the following formula (1) or (2) or a salt thereof:

in which, each Q independently represents a halogen atom, each R¹¹ and R¹² independently represents an alkyl group substituted with an ionic hydrophilic group, and A¹ is a group represented by the following formula (A1-1), a group represented by the following formula (A1-2), a C1-C3 alkoxy-substituted alkylamino group, a C1-C6 alkyl-monosubstituted amino group, a C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups, a group represented by the following formula (A1-3), a group represented by the following formula (A1-4), or a cyclic amine group,

in which, R^(A11) represents a branched alkylene group, and the symbol “*” indicates a position of attachment to a triazine ring,

In which, n represents an integer of 1 to 6, and the symbol “*” indicates a position of attachment to the triazine ring,

in which, m represents an integer of 1 to 6, n represents an integer of 1 to 5, and the symbol “*” indicates a position of attachment to the triazine ring,

in which, n represents an integer of 2 to 6, and the symbol “*” indicates a position of attachment to the triazine ring,

in which, each Q²¹ to Q²⁴ independently represents a halogen atom, and each R²¹ to R²⁴ independently represents an alkyl group substituted with an ionic hydrophilic group, and A² represents a divalent group.

2) The compound or a salt thereof according to 1), in which the compound represented by the formula (1) is represented by the following formula (1-1):

in which, Q and A¹ have the same meanings as defined in the formula (1), and each x independently represents an integer of 2 to 4.

3) The compound or a salt thereof according to 2), in which in the formula (1-1), Q is a chlorine atom.

4) The compound or a salt thereof according to 2) or 3), in which in the formula (1-1), x is 3.

5) The compound or a salt thereof according to 1), in which the compound represented by the formula (1) is represented by any of the following formulae (1-11) to (1-15):

6) The compound or a salt thereof according to any one of 1) to 4), in which in the formula (A1-2), n is 2.

7) The compound or a salt thereof according to 1), in which the compound represented by the formula (1) is represented by the following formula (1-16).

8) The compound or a salt thereof according to 2), in which in the the formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a group represented by the following formula (A1-5):

in which, R^(A12) represents a C1-C3 alkyl group, n represents an integer of 1 to 6, and the symbol “*” indicates a position of attachment to the triazine ring.

9) The compound or a salt thereof according to 8), in which in the formula (A1-5), n is 3.

10) The compound or a salt thereof according to 2), in which in the formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a C1-C4 alkyl-monosubstituted amino group.

11) The compound or a salt thereof according to 10), wherein in the the formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a linear C1-C4 alkyl-monosubstituted amino group.

12) The compound or a salt thereof according to 2), wherein in the formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a group represented by the following formula (A1-6):

in which, R^(A13) represents a C2-C6 alkyl group having two or more hydroxy groups, and the symbol “*” indicates a position of attachment to the triazine ring.

13) The compound or a salt thereof according to 12), in which in the formula (A1-6), R^(A13) is a C2-C4 alkyl group having two hydroxy groups.

14) The compound or a salt thereof according to any one of 1) to 4), in which in the formula (1), A¹ is a group represented by following formula (A1-7) or (A1-8):

in which, the symbol “*” indicates a position of attachment to the triazine ring.

15) The compound or a salt thereof according to any one of 1) to 4), in which in the formula (A1-3), m is 2.

16) The compound or a salt thereof according to 1), in which the compound represented by the formula (1) is represented by the following formula (1-17) or (1-18):

17) The compound or a salt thereof according to 2), in which in the formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a group represented by the formula (1-4) wherein n is 3.

18) The compound or a salt thereof according to 2), in which in the formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a group represented by the following formula (A1-9):

in which, each R^(A14) to R^(A21) independently represents a hydrogen atom or a substituent, and the symbol “*” indicates a position of attachment to the triazine ring.

19) The compound or a salt thereof according to 18), in which in the formula (A1-9), R^(A14) to R^(A21) are hydrogen atoms.

20) The compound or a salt thereof according to 1), in which the compound represented by the formula (2) is represented by the following formula (2-1):

in which, Q²¹ to Q²⁴ and A² have the same meanings as defined in the formula (2), each x independently represents an integer of 2 to 4.

21) The compound or a salt thereof according to 20), in which in the formula (2-1), Q²¹ to Q²⁴ are chlorine atoms.

22) The compound or a salt thereof according to 20) or 21), in which in the formula (2-1), x is 3.

23) The compound or a salt thereof according to 20), in which in the formula (2-1), Q²¹ to Q²⁴ are chlorine atoms, x is 3, and A² is a 1,4-piperazinediyl group.

24) An ink including the compound or a salt thereof according to any one of 1) to 23).

25) The ink according to 24), further including a water-soluble organic solvent.

26) Use of the ink according to 24) or 25) for ink-jet recording.

27) An ink-jet recording method, including discharging a droplet of the ink according to 24) or 25) in response to a recording signal to allow for attachment to a recording medium.

28) An ink-jet recording method according to 27), in which the recording medium is plain paper or a sheet having an ink receiving layer.

29) A recording medium to which either

(a) the compound or a salt thereof according to any one of 1) to 23) or

(b) the ink according to 24) or 25) is attached.

30) An ink-jet printer loaded with a container containing the ink according to 24) or 25).

Effects of the Invention

The present invention can provide a water-soluble azo compound capable of producing a recorded image with excellent light resistance, and a yellow ink containing the above compound for use in various types of recording, in particular for an ink-jet recording purpose.

PREFERRED MODE FOR CARRYING OUT THE INVENTION

The water-soluble azo compound according to the present invention (the compound or a salt thereof represented by the above formula (1) or (2)) is a water-soluble yellow coloring matter. Unless otherwise specifically stated, among ionic hydrophilic groups, acidic functional groups are shown in a form of a free acid. This also applies to Examples. Further, unless otherwise specifically stated, the term “compound” having an ionic hydrophilic group as used herein is meant to encompass both a “compound or a salt thereof”. Moreover, unless otherwise specifically stated, the terms “%” and “part” as used herein are based on mass. This also applies to Examples.

[Compound Represented by Formula (1)]

In the above formula (1), Q represents a halogen atom. Halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom or a chlorine atom is preferred, and a chlorine atom is more preferred.

In the above formula (1), each R¹¹ and R¹² independently represents an alkyl group substituted with an ionic hydrophilic group. The carbon number of an alkyl group moiety is preferably 2 to 4, and more preferably 3. Ionic hydrophilic groups include a group selected from a sulfo group, a carboxy group, a phospho group, and a quaternary ammonium group. Among these, preferred is a group selected from a sulfo group, a carboxy group, and a phospho group. More preferred is a group selected from a sulfo group and a carboxy group. Even more preferred is a sulfo group. There is no particular limitation for the number of substitutions in an ionic hydrophilic group, but it is usually 1 to 5, preferably 1 to 4, more preferably 1 to 3, even more preferably 1 or 2, and in particular preferably 1.

Specific examples of an alkyl group substituted with an ionic hydrophilic group include, for example, a sulfomethyl group, a sulfoethyl group, a 2,3-disulfopropyl group, a 3-sulfopropyl group, a 4-sulfobutyl group, a 5-sulfopentyl group, a 6-sulfohexyl group, a 7-sulfoheptyl group, an 8-sulfooctyl group, a carboxymethyl group, a carboxyethyl group, a 3-carboxypropyl group, a 4-carboxybutyl group, a 5-carboxypentyl group, a 6-carboxyhexyl group, a 7-carboxyheptyl group, an 8-carboxyoctyl group, a phosphomethyl group, a phosphoethyl group, a 3-phosphopropyl group, a 4-phosphobutyl group, a 5-phosphopentyl group, a 6-phosphohexyl group, a 7-phosphoheptyl group, an 8-phosphooctyl group, a trimethylammoniummethyl group, a trimethylammoniumethyl group, 3-trimethylammoniumpropyl group, a 4-trimethylammoniumbutyl group, a 5-trimethylammoniumpentyl group, a 6-trimethylammoniumhexyl group, a 7-trimethylammoniumheptyl group, an 8-trimethylammoniumoctyl group, a 2-methyl-3-sulfopropyl group, a 2,2-dimethyl-3-sulfopropyl group, a 4-sulfocyclohexyl group, a 2,5-disulfocyclohexylmethyl group and the like. A 3-sulfopropyl group is preferred.

In the above formula (1), A¹ represents a group represented by the above formula (A1-1), a group represented by the above formula (A1-2), a C1-C3 alkoxy-substituted alkylamino group, a C1-C6 alkyl-monosubstituted amino group, a C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups, a group represented by the above formula (A1-3), a group represented by the above formula (A1-4), or a cyclic amine group. A¹ will be described in detail below.

Among the compounds represented by the above formula (1), preferred is a compound represented by the above formula (1-1). In the above formula (1-1), Q and A¹ have the same meanings as defined in the above formula (1), including those preferred and the like. In the above formula (1-1), each x independently represents an integer of 2 to 4, and preferably 3.

(Group Represented by Formula (A1-1))

In the above formula (A1-1), R^(A11) represents a branched alkylene group. The carbon number of R^(A11) is usually 2 to 20, preferably 3 to 12, more preferably 3 to 8, and even more preferably 3 to 6. Specific examples of a group represented by the above formula (A1-1) include, for example, an isopropylene group, an isobutylene group, an s-butylene group, a t-butylene group, a 1-methyl-n-butylene group, a 2-methyl-n-butylene group, a 3-methyl-n-butylene group, a 1,1-dimethyl-n-propylene group, a 1,2-dimethyl-n-propylene group, a 2,2-dimethyl-n-propylene group, a 1-ethyl-n-propylene group, an n-hexylene group, a 1-methyl-n-pentylene group, a 2-methyl-n-pentylene group, a 3-methyl-n-pentylene group, a 4-methyl-n-pentylene group, a 1,1-dimethyl-n-butylene group, a 1,2-dimethyl-n-butylene group, a 1,3-dimethyl-n-butylene group, a 2,2-dimethyl-n-butylene group, a 2,3-dimethyl-n-butylene group, a 3,3-dimethyl-n-butylene group, a 1-ethyl-n-butylene group, a 2-ethyl-n-butylene group, a 1,1,2-trimethyl-n-propylene group, a 1,2,2-trimethyl-n-propylene group, a 1-ethyl-1-methyl-n-propylene group, a 1-ethyl-2-methyl-n-propylene group and the like. An isobutylene group or a 3-methyl-n-butylene group is preferred.

When A¹ in the above formula (1) is a group represented by the above formula (A1-1), preferred compounds include, for example, those represented by the above formulae (1-11) to (1-15).

(Group Represented by Formula (A1-2))

In the above formula (A1-2), n represents an integer of 1 to 6, preferably an integer of 2 to 5, and more preferably 2.

Specific examples of a compound in which A¹ in the above formula (1) is a group represented by the above formula (A1-2) are shown in the Tables 1 and 2 below. However, the present invention shall not be limited to these specific examples. Abbreviations in Tables 1 and 2 have the following meanings.

2-SEt: 2-sulfoethyl (*—CH₂CH₂—SO₃H)

3-S^(n)Pr: 3-sulfo-n-propyl (*—CH₂CH₂CH₂—SO₃H)

4-S^(n)Bu: 3-sulfo-n-butyl (*—CH₂CH₂CH₂CH₂—SO₃H)

The symbol “*” in the above formulae indicates a position of attachment to the oxygen atom.

TABLE 1 No. Q R¹¹ R¹² A¹  1 Cl 2-SEt 2-SEt Formula (A1-2), n = 1  2 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 1  3 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 1  4 Cl 2-SEt 2-SEt Formula (A1-2), n = 2  5 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 2  6 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 2  7 Cl 2-SEt 2-SEt Formula (A1-2), n = 3  8 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 3  9 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 3 10 Cl 2-SEt 2-SEt Formula (A1-2), n = 4 11 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 4 12 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 4 13 Cl 2-SEt 2-SEt Formula (A1-2), n = 5 14 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 5 15 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 5 16 Cl 2-SEt 2-SEt Formula (A1-2), n = 6 17 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 6 18 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 6 19 Br 2-SEt 2-SEt Formula (A1-2), n = 1 20 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 1 21 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 1 22 Br 2-SEt 2-SEt Formula (A1-2), n = 2 23 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 2 24 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 2 25 Br 2-SEt 2-SEt Formula (A1-2), n = 3 26 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 3 27 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 3 28 Br 2-SEt 2-SEt Formula (A1-2), n = 4 29 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 4 30 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 4

TABLE 2 No. Q R¹¹ R¹² A¹ 31 Br 2-SEt 2-SEt Formula (A1-2), n = 5 32 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 5 33 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 5 34 Br 2-SEt 2-SEt Formula (A1-2), n = 6 35 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 6 36 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 6 37 F 2-SEt 2-SEt Formula (A1-2), n = 1 38 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 1 39 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 1 40 F 2-SEt 2-SEt Formula (A1-2), n = 2 41 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 2 42 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 2 43 F 2-SEt 2-SEt Formula (A1-2), n = 3 44 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 3 45 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 3 46 F 2-SEt 2-SEt Formula (A1-2), n = 4 47 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 4 48 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 4 49 F 2-SEt 2-SEt Formula (A1-2), n = 5 50 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 5 51 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 5 52 F 2-SEt 2-SEt Formula (A1-2), n = 6 53 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-2), n = 6 54 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-2), n = 6

When A¹ in the above formula (1) is a group represented by the above formula (A1-2), preferred compounds include, for example, one represented by the above formula (1-16).

(C1-C3 Alkoxy-Substituted Alkylamino Group)

The carbon number of an alkyl moiety in a C1-C3 alkoxy-substituted alkylamino group is preferably 1 to 6, more preferably 2 to 5, and even more preferably 3. The number of substitutions in a C1-C3 alkoxy group of a C1-C3 alkoxy-substituted alkylamino group is usually 1 or 2, preferably 1.

Among C1-C3 alkoxy-substituted alkylamino groups, preferred is a group represented by the above formula (A1-5). In the above formula (A1-5), R^(A12) represents a C1-C3 alkyl group. Further, in the above formula (A1-5), n represents an integer of 1 to 6, preferably an integer of 2 to 5, and more preferably 3.

Specific examples of a compound in which A¹ in the above formula (1) is a C1-C3 alkoxy-substituted alkylamino group are shown in the Tables 3 to 14 below. However, the present invention shall not be limited to these specific examples. Abbreviations in Tables 3 to 14 have the following meanings.

SMe: sulfomethyl (*—CH₂—SO₃H)

2-SEt: 2-sulfoethyl (*—CH₂CH₂—SO₃H)

3-S^(n)Pr: 3-sulfo-n-propyl (*—CH₂CH₂CH₂—SO₃H)

4-S^(n)Bu: 3-sulfo-n-butyl (*—CH₂CH₂CH₂CH₂—SO₃H)

The symbol “*” in the above formulae indicates a position of attachment to the oxygen atom.

TABLE 3 No. Q R¹¹ R¹² A¹  1 Cl SMe SMe Formula (A1-5), n = 1, R^(A12) = CH₃  2 Cl SMe 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₃  3 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₃  4 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃  5 Cl 2-SEt 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₃  6 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₃  7 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃  8 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₃  9 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 10 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 11 Cl SMe SMe Formula (A1-5), n = 2, R^(A12) = CH₃ 12 Cl SMe 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₃ 13 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₃ 14 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 15 Cl 2-SEt 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₃ 16 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₃ 17 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 18 Cl 3-SnPr 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₃ 19 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 20 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 21 Cl SMe SMe Formula (A1-5), n = 3, R^(A12) = CH₃ 22 Cl SMe 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₃ 23 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₃ 24 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃ 25 Cl 2-SEt 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₃ 26 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₃ 27 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃ 28 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₃ 29 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃ 30 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃

TABLE 4 No. Q R¹¹ R¹² A¹ 31 Cl SMe SMe Formula (A1-5), n = 4, R^(A12) = CH₃ 32 Cl SMe 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₃ 33 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₃ 34 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 35 Cl 2-SEt 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₃ 36 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₃ 37 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 38 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₃ 39 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 40 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 41 Cl SMe SMe Formula (A1-5), n = 5, R^(A12) = CH₃ 42 Cl SMe 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₃ 43 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₃ 44 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 45 Cl 2-SEt 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₃ 46 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₃ 47 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 48 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₃ 49 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 50 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 51 Cl SMe SMe Formula (A1-5), n = 6, R^(A12) = CH₃ 52 Cl SMe 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₃ 53 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₃ 54 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃ 55 Cl 2-SEt 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₃ 56 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₃ 57 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃ 58 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₃ 59 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃ 60 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃

TABLE 5 No. Q R¹¹ R¹² A¹ 61 Cl SMe SMe Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 62 Cl SMe 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 63 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 64 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 65 Cl 2-SEt 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 66 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 67 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 68 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 69 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 70 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 71 Cl SMe SMe Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 72 Cl SMe 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 73 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 74 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 75 Cl 2-SEt 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 76 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 77 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 78 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 79 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 80 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 81 Cl SMe SMe Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 82 Cl SMe 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 83 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 84 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 85 Cl 2-SEt 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 86 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 87 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 88 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 89 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 90 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃

TABLE 6 No. Q R¹¹ R¹² A¹  91 Cl SMe SMe Formula (A1-5), n = 4, R^(A12) = CH₂CH₃  92 Cl SMe 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₂CH₃  93 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₂CH₃  94 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃  95 Cl 2-SEt 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₂CH₃  96 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₂CH₃  97 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃  98 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₂CH₃  99 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 100 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 101 Cl SMe SMe Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 102 Cl SMe 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 103 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 104 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 105 Cl 2-SEt 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 106 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 107 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 108 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 109 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 110 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 111 Cl SMe SMe Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 112 Cl SMe 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 113 Cl SMe 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 114 Cl SMe 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 115 Cl 2-SEt 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 116 Cl 2-SEt 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 117 Cl 2-SEt 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 118 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 119 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 120 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃

TABLE 7 No. Q R¹¹ R¹² A¹ 121 Br SMe SMe Formula (A1-5), n = 1, R^(A12) = CH₃ 122 Br SMe 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₃ 123 Br SMe 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₃ 124 Br SMe 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 125 Br 2-SEt 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₃ 126 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₃ 127 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 128 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₃ 129 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 130 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 131 Br SMe SMe Formula (A1-5), n = 2, R^(A12) = CH₃ 132 Br SMe 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₃ 133 Br SMe 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₃ 134 Br SMe 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 135 Br 2-SEt 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₃ 136 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₃ 137 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 138 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₃ 139 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 140 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 141 Br SMe SMe Formula (A1-5), n = 3, R^(A12) = CH₃ 142 Br SMe 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₃ 143 Br SMe 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₃ 144 Br SMe 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃ 145 Br 2-SEt 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₃ 146 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₃ 147 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃ 148 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₃ 149 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃ 150 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃

TABLE 8 No. Q R¹¹ R¹² A¹ 151 Br SMe SMe Formula (A1-5), n = 4, R^(A12) = CH₃ 152 Br SMe 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₃ 153 Br SMe 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₃ 154 Br SMe 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 155 Br 2-SEt 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₃ 156 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₃ 157 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 158 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₃ 159 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 160 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 161 Br SMe SMe Formula (A1-5), n = 5, R^(A12) = CH₃ 162 Br SMe 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₃ 163 Br SMe 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₃ 164 Br SMe 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 165 Br 2-SEt 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₃ 166 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₃ 167 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 168 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₃ 169 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 170 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 171 Br SMe SMe Formula (A1-5), n = 6, R^(A12) = CH₃ 172 Br SMe 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₃ 173 Br SMe 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₃ 174 Br SMe 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃ 175 Br 2-SEt 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₃ 176 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₃ 177 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃ 178 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₃ 179 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃ 180 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃

TABLE 9 No. Q R¹¹ R¹² A¹ 181 Br SMe SMe Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 182 Br SMe 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 183 Br SMe 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 184 Br SMe 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 185 Br 2-SEt 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 186 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 187 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 188 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 189 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 190 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 191 Br SMe SMe Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 192 Br SMe 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 193 Br SMe 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 194 Br SMe 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 195 Br 2-SEt 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 196 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 197 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 198 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 199 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 200 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 201 Br SMe SMe Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 202 Br SMe 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 203 Br SMe 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 204 Br SMe 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 205 Br 2-SEt 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 206 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 207 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 208 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 209 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 210 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃

TABLE 10 No. Q R¹¹ R¹² A¹ 211 Br SMe SMe Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 212 Br SMe 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 213 Br SMe 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 214 Br SMe 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 215 Br 2-SEt 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 216 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 217 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 218 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 219 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 220 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 221 Br SMe SMe Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 222 Br SMe 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 223 Br SMe 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 224 Br SMe 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 225 Br 2-SEt 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 226 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 227 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 228 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 229 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 230 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 231 Br SMe SMe Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 232 Br SMe 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 233 Br SMe 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 234 Br SMe 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 235 Br 2-SEt 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 236 Br 2-SEt 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 237 Br 2-SEt 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 238 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 239 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 240 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃

TABLE 11 No. Q R¹¹ R¹² A¹ 241 F SMe SMe Formula (A1-5), n = 1, R^(A12) = CH₃ 242 F SMe 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₃ 243 F SMe 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₃ 244 F SMe 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 245 F 2-SEt 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₃ 246 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₃ 247 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 248 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₃ 249 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 250 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₃ 251 F SMe SMe Formula (A1-5), n = 2, R^(A12) = CH₃ 252 F SMe 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₃ 253 F SMe 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₃ 254 F SMe 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 255 F 2-SEt 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₃ 256 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₃ 257 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 258 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₃ 259 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 260 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₃ 261 F SMe SMe Formula (A1-5), n = 3, R^(A12) = CH₃ 262 F SMe 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₃ 263 F SMe 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₃ 264 F SMe 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃ 265 F 2-SEt 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₃ 266 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₃ 267 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃ 268 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₃ 269 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃ 270 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₃

TABLE 12 No. Q R¹¹ R¹² A¹ 271 F SMe SMe Formula (A1-5), n = 4, R^(A12) = CH₃ 272 F SMe 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₃ 273 F SMe 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₃ 274 F SMe 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 275 F 2-SEt 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₃ 276 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₃ 277 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 278 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₃ 279 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 280 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₃ 281 F SMe SMe Formula (A1-5), n = 5, R^(A12) = CH₃ 282 F SMe 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₃ 283 F SMe 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₃ 284 F SMe 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 285 F 2-SEt 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₃ 286 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₃ 287 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 288 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₃ 289 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 290 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₃ 291 F SMe SMe Formula (A1-5), n = 6, R^(A12) = CH₃ 292 F SMe 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₃ 293 F SMe 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₃ 294 F SMe 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃ 295 F 2-SEt 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₃ 296 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₃ 297 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃ 298 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₃ 299 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃ 300 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₃

TABLE 13 No. Q R¹¹ R¹² A¹ 301 F SMe SMe Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 302 F SMe 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 303 F SMe 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 304 F SMe 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 305 F 2-SEt 2-SEt Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 306 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 307 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 308 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 309 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 310 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 1, R^(A12) = CH₂CH₃ 311 F SMe SMe Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 312 F SMe 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 313 F SMe 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 314 F SMe 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 315 F 2-SEt 2-SEt Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 316 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 317 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 318 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 319 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 320 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 2, R^(A12) = CH₂CH₃ 321 F SMe SMe Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 322 F SMe 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 323 F SMe 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 324 F SMe 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 325 F 2-SEt 2-SEt Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 326 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 327 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 328 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 329 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃ 330 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 3, R^(A12) = CH₂CH₃

TABLE 14 No. Q R¹¹ R¹² A¹ 331 F SMe SMe Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 332 F SMe 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 333 F SMe 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 334 F SMe 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 335 F 2-SEt 2-SEt Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 336 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 337 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 338 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 339 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 340 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 4, R^(A12) = CH₂CH₃ 341 F SMe SMe Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 342 F SMe 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 343 F SMe 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 344 F SMe 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 345 F 2-SEt 2-SEt Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 346 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 347 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 348 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 349 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 350 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 5, R^(A12) = CH₂CH₃ 351 F SMe SMe Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 352 F SMe 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 353 F SMe 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 354 F SMe 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 355 F 2-SEt 2-SEt Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 356 F 2-SEt 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 357 F 2-SEt 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 358 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 359 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃ 360 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-5), n = 6, R^(A12) = CH₂CH₃

When A¹ in the above formula (1) is a C1-C3 alkoxy-substituted alkylamino group, preferred compounds include, for example, one in which in the above formula (1-1), Q is a chlorine atom, x is 3, A¹ is a group represented by the above formula (A1-5), and n in the above formula (A1-5) is 3.

(C1-C6 Alkyl-Monosubstituted Amino Group)

Specific examples of a C1-C6 alkyl-monosubstituted amino group include, for example, a monomethylamino group, a monoethylamino group, a mono-n-propylamino group, a monoisopropylamino group, a mono-n-butylamino group, a mono-s-butylamino group, a mono-t-butylamino group, a mono-n-pentylamino group, a mono-n-hexylamino group and the like. Among these, a C1-C4 alkyl-monosubstituted amino group is preferred, and a linear C1-C4 alkyl-monosubstituted amino group is more preferred such as a monomethylamino group, a monoethylamino group, a mono-n-propylamino group, a mono-n-butylamino group.

Specific examples of a compound in which A¹ in the above formula (1) is a C1-C6 alkyl-monosubstituted amino group are shown in Tables 15 to 20 below. However, the present invention shall not be limited to these specific examples. Abbreviations in Tables 15 to 20 have the following meanings.

SMe: sulfomethyl (*—CH₂—SO₃H)

2-SEt: 2-sulfoethyl (*—CH₂CH₂—SO₃H)

3-S^(n)Pr: 3-sulfo-n-propyl (*—CH₂CH₂CH₂—SO₃H)

4-S^(n)Bu: 3-sulfo-n-butyl (*—CH₂CH₂CH₂CH₂—SO₃H)

The symbol “*” in the above formulae indicates a position of attachment to the oxygen atom.

TABLE 15 No. Q R¹¹ R¹² A¹ 1 Cl SMe SMe NHCH₃ 2 Cl SMe 2-SEt NHCH₃ 3 Cl SMe 3-S^(n)Pr NHCH₃ 4 Cl SMe 4-S^(n)Bu NHCH₃ 5 Cl 2-SEt 2-SEt NHCH₃ 6 Cl 2-SEt 3-S^(n)Pr NHCH₃ 7 Cl 2-SEt 4-S^(n)Bu NHCH₃ 8 Cl 3-S^(n)Pr 3-S^(n)Pr NHCH₃ 9 Cl 3-S^(n)Pr 4-S^(n)Bu NHCH₃ 10 Cl 4-S^(n)Bu 4-S^(n)Bu NHCH₃ 11 Cl SMe SMe NHC₂H₅ 12 Cl SMe 2-SEt NHC₂H₅ 13 Cl SMe 3-S^(n)Pr NHC₂H₅ 14 Cl SMe 4-S^(n)Bu NHC₂H₅ 15 Cl 2-SEt 2-SEt NHC₂H₅ 16 Cl 2-SEt 3-S^(n)Pr NHC₂H₅ 17 Cl 2-SEt 4-S^(n)Bu NHC₂H₅ 18 Cl 3-S^(n)Pr 3-S^(n)Pr NHC₂H₅ 19 Cl 3-S^(n)Pr 4-S^(n)Bu NHC₂H₅ 20 Cl 4-S^(n)Bu 4-S^(n)Bu NHC₂H₅ 21 Cl SMe SMe NHC₃H₇ 22 Cl SMe 2-SEt NHC₃H₇ 23 Cl SMe 3-S^(n)Pr NHC₃H₇ 24 Cl SMe 4-S^(n)Bu NHC₃H₇ 25 Cl 2-SEt 2-SEt NHC₃H₇ 26 Cl 2-SEt 3-S^(n)Pr NHC₃H₇ 27 Cl 2-SEt 4-S^(n)Bu NHC₃H₇ 28 Cl 3-S^(n)Pr 3-S^(n)Pr NHC₃H₇ 29 Cl 3-S^(n)Pr 4-S^(n)Bu NHC₃H₇ 30 Cl 4-S^(n)Bu 4-S^(n)Bu NHC₃H₇

TABLE 16 No. Q R¹¹ R¹² A¹ 31 Cl SMe SMe NHC₄H₉ 32 Cl SMe 2-SEt NHC₄H₉ 33 Cl SMe 3-S^(n)Pr NHC₄H₉ 34 Cl SMe 4-S^(n)Bu NHC₄H₉ 35 Cl 2-SEt 2-SEt NHC₄H₉ 36 Cl 2-SEt 3-S^(n)Pr NHC₄H₉ 37 Cl 2-SEt 4-S^(n)Bu NHC₄H₉ 38 Cl 3-S^(n)Pr 3-S^(n)Pr NHC₄H₉ 39 Cl 3-S^(n)Pr 4-S^(n)Bu NHC₄H₉ 40 Cl 4-S^(n)Bu 4-S^(n)Bu NHC₄H₉ 41 Cl SMe SMe NHC₅H₁₁ 42 Cl SMe 2-SEt NHC₅H₁₁ 43 Cl SMe 3-S^(n)Pr NHC₅H₁₁ 44 Cl SMe 4-S^(n)Bu NHC₅H₁₁ 45 Cl 2-SEt 2-SEt NHC₅H₁₁ 46 Cl 2-SEt 3-S^(n)Pr NHC₅H₁₁ 47 Cl 2-SEt 4-S^(n)Bu NHC₅H₁₁ 48 Cl 3-S^(n)Pr 3-S^(n)Pr NHC₅H₁₁ 49 Cl 3-S^(n)Pr 4-S^(n)Bu NHC₅H₁₁ 50 Cl 4-S^(n)Bu 4-S^(n)Bu NHC₅H₁₁ 51 Cl SMe SMe NHC₆H₁₃ 52 Cl SMe 2-SEt NHC₆H₁₃ 53 Cl SMe 3-S^(n)Pr NHC₆H₁₃ 54 Cl SMe 4-S^(n)Bu NHC₆H₁₃ 55 Cl 2-SEt 2-SEt NHC₆H₁₃ 56 Cl 2-SEt 3-S^(n)Pr NHC₆H₁₃ 57 Cl 2-SEt 4-S^(n)Bu NHC₆H₁₃ 58 Cl 3-S^(n)Pr 3-S^(n)Pr NHC₆H₁₃ 59 Cl 3-S^(n)Pr 4-S^(n)Bu NHC₆H₁₃ 60 Cl 4-S^(n)Bu 4-S^(n)Bu NHC₆H₁₃

TABLE 17 No. Q R¹¹ R¹² A¹ 61 Br SMe SMe NHCH₃ 62 Br SMe 2-SEt NHCH₃ 63 Br SMe 3-S^(n)Pr NHCH₃ 64 Br SMe 4-S^(n)Bu NHCH₃ 65 Br 2-SEt 2-SEt NHCH₃ 66 Br 2-SEt 3-S^(n)Pr NHCH₃ 67 Br 2-SEt 4-S^(n)Bu NHCH₃ 68 Br 3-S^(n)Pr 3-S^(n)Pr NHCH₃ 69 Br 3-S^(n)Pr 4-S^(n)Bu NHCH₃ 70 Br 4-S^(n)Bu 4-S^(n)Bu NHCH₃ 71 Br SMe SMe NHC₂H₅ 72 Br SMe 2-SEt NHC₂H₅ 73 Br SMe 3-S^(n)Pr NHC₂H₅ 74 Br SMe 4-S^(n)Bu NHC₂H₅ 75 Br 2-SEt 2-SEt NHC₂H₅ 76 Br 2-SEt 3-S^(n)Pr NHC₂H₅ 77 Br 2-SEt 4-S^(n)Bu NHC₂H₅ 78 Br 3-S^(n)Pr 3-S^(n)Pr NHC₂H₅ 79 Br 3-S^(n)Pr 4-S^(n)Bu NHC₂H₅ 80 Br 4-S^(n)Bu 4-S^(n)Bu NHC₂H₅ 81 Br SMe SMe NHC₃H₇ 82 Br SMe 2-SEt NHC₃H₇ 83 Br SMe 3-S^(n)Pr NHC₃H₇ 84 Br SMe 4-S^(n)Bu NHC₃H₇ 85 Br 2-SEt 2-SEt NHC₃H₇ 86 Br 2-SEt 3-S^(n)Pr NHC₃H₇ 87 Br 2-SEt 4-S^(n)Bu NHC₃H₇ 88 Br 3-S^(n)Pr 3-S^(n)Pr NHC₃H₇ 89 Br 3-S^(n)Pr 4-S^(n)Bu NHC₃H₇ 90 Br 4-S^(n)Bu 4-S^(n)Bu NHC₃H₇

TABLE 18 No. Q R¹¹ R¹² A¹ 91 Br SMe SMe NHC₄H₉ 92 Br SMe 2-SEt NHC₄H₉ 93 Br SMe 3-S^(n)Pr NHC₄H₉ 94 Br SMe 4-S^(n)Bu NHC₄H₉ 95 Br 2-SEt 2-SEt NHC₄H₉ 96 Br 2-SEt 3-S^(n)Pr NHC₄H₉ 97 Br 2-SEt 4-S^(n)Bu NHC₄H₉ 98 Br 3-S^(n)Pr 3-S^(n)Pr NHC₄H₉ 99 Br 3-S^(n)Pr 4-S^(n)Bu NHC₄H₉ 100 Br 4-S^(n)Bu 4-S^(n)Bu NHC₄H₉ 101 Br SMe SMe NHC₅H₁₁ 102 Br SMe 2-SEt NHC₅H₁₁ 103 Br SMe 3-S^(n)Pr NHC₅H₁₁ 104 Br SMe 4-S^(n)Bu NHC₅H₁₁ 105 Br 2-SEt 2-SEt NHC₅H₁₁ 106 Br 2-SEt 3-S^(n)Pr NHC₅H₁₁ 107 Br 2-SEt 4-S^(n)Bu NHC₅H₁₁ 108 Br 3-S^(n)Pr 3-S^(n)Pr NHC₅H₁₁ 109 Br 3-S^(n)Pr 4-S^(n)Bu NHC₅H₁₁ 110 Br 4-S^(n)Bu 4-S^(n)Bu NHC₅H₁₁ 111 Br SMe SMe NHC₆H₁₃ 112 Br SMe 2-SEt NHC₆H₁₃ 113 Br SMe 3-S^(n)Pr NHC₆H₁₃ 114 Br SMe 4-S^(n)Bu NHC₆H₁₃ 115 Br 2-SEt 2-SEt NHC₆H₁₃ 116 Br 2-SEt 3-S^(n)Pr NHC₆H₁₃ 117 Br 2-SEt 4-S^(n)Bu NHC₆H₁₃ 118 Br 3-S^(n)Pr 3-S^(n)Pr NHC₆H₁₃ 119 Br 3-S^(n)Pr 4-S^(n)Bu NHC₆H₁₃ 120 Br 4-S^(n)Bu 4-S^(n)Bu NHC₆H₁₃

TABLE 19 No. Q R¹¹ R¹² A¹ 121 F SMe SMe NHCH₃ 122 F SMe 2-SEt NHCH₃ 123 F SMe 3-S^(n)Pr NHCH₃ 124 F SMe 4-S^(n)Bu NHCH₃ 125 F 2-SEt 2-SEt NHCH₃ 126 F 2-SEt 3-S^(n)Pr NHCH₃ 127 F 2-SEt 4-S^(n)Bu NHCH₃ 128 F 3-S^(n)Pr 3-S^(n)Pr NHCH₃ 129 F 3-S^(n)Pr 4-S^(n)Bu NHCH₃ 130 F 4-S^(n)Bu 4-S^(n)Bu NHCH₃ 131 F SMe SMe NHC₂H₅ 132 F SMe 2-SEt NHC₂H₅ 133 F SMe 3-S^(n)Pr NHC₂H₅ 134 F SMe 4-S^(n)Bu NHC₂H₅ 135 F 2-SEt 2-SEt NHC₂H₅ 136 F 2-SEt 3-S^(n)Pr NHC₂H₅ 137 F 2-SEt 4-S^(n)Bu NHC₂H₅ 138 F 3-S^(n)Pr 3-S^(n)Pr NHC₂H₅ 139 F 3-S^(n)Pr 4-S^(n)Bu NHC₂H₅ 140 F 4-S^(n)Bu 4-S^(n)Bu NHC₂H₅ 141 F SMe SMe NHC₃H₇ 142 F SMe 2-SEt NHC₃H₇ 143 F SMe 3-S^(n)Pr NHC₃H₇ 144 F SMe 4-S^(n)Bu NHC₃H₇ 145 F 2-SEt 2-SEt NHC₃H₇ 146 F 2-SEt 3-S^(n)Pr NHC₃H₇ 147 F 2-SEt 4-S^(n)Bu NHC₃H₇ 148 F 3-S^(n)Pr 3-S^(n)Pr NHC₃H₇ 149 F 3-S^(n)Pr 4-S^(n)Bu NHC₃H₇ 150 F 4-S^(n)Bu 4-S^(n)Bu NHC₃H₇

TABLE 20 No. Q R¹¹ R¹² A¹ 151 F SMe SMe NHC₄H₉ 152 F SMe 2-SEt NHC₄H₉ 153 F SMe 3-S^(n)Pr NHC₄H₉ 154 F SMe 4-S^(n)Bu NHC₄H₉ 155 F 2-SEt 2-SEt NHC₄H₉ 156 F 2-SEt 3-S^(n)Pr NHC₄H₉ 157 F 2-SEt 4-S^(n)Bu NHC₄H₉ 158 F 3-S^(n)Pr 3-S^(n)Pr NHC₄H₉ 159 F 3-S^(n)Pr 4-S^(n)Bu NHC₄H₉ 160 F 4-S^(n)Bu 4-S^(n)Bu NHC₄H₉ 161 F SMe SMe NHC₅H₁₁ 162 F SMe 2-SEt NHC₅H₁₁ 163 F SMe 3-S^(n)Pr NHC₅H₁₁ 164 F SMe 4-S^(n)Bu NHC₅H₁₁ 165 F 2-SEt 2-SEt NHC₅H₁₁ 166 F 2-SEt 3-S^(n)Pr NHC₅H₁₁ 167 F 2-SEt 4-S^(n)Bu NHC₅H₁₁ 168 F 3-S^(n)Pr 3-S^(n)Pr NHC₅H₁₁ 169 F 3-S^(n)Pr 4-S^(n)Bu NHC₅H₁₁ 170 F 4-S^(n)Bu 4-S^(n)Bu NHC₅H₁₁ 171 F SMe SMe NHC₆H₁₃ 172 F SMe 2-SEt NHC₆H₁₃ 173 F SMe 3-S^(n)Pr NHC₆H₁₃ 174 F SMe 4-S^(n)Bu NHC₆H₁₃ 175 F 2-SEt 2-SEt NHC₆H₁₃ 176 F 2-SEt 3-S^(n)Pr NHC₆H₁₃ 177 F 2-SEt 4-S^(n)Bu NHC₆H₁₃ 178 F 3-S^(n)Pr 3-S^(n)Pr NHC₆H₁₃ 179 F 3-S^(n)Pr 4-S^(n)Bu NHC₆H₁₃ 180 F 4-S^(n)Bu 4-S^(n)Bu NHC₆H₁₃

When A¹ in the above formula (1) is a C1-C6 alkyl-monosubstituted amino group, preferred compounds include, for example, one in which in the above formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a C1-C4 alkyl-monosubstituted amino group. More preferred compounds include, for example, one in which in the above formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a linear C1-C4 alky-monosubstituted amino group.

(C2-C6 Alkyl-Monosubstituted Amino Group Having Two or More Hydroxy Groups)

The number of substitutions in a hydroxy group of a C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups is usually 2 or 3, and preferably 2. The C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups is preferably a group represented by the above formula (A1-6). In the above formula (A1-6), R^(A13) represents a C2-C6 alkyl group having two or more hydroxy groups, preferably a C2-C4 alkyl group having two hydroxy groups.

Specific examples of a C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups include, for example, a linear C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups such as a 1,2-dihydroxyethylamino group, a 1,1-dihydroxyethylamino group, a 1,2-dihydroxypropylamino group, a 1,2-dihydroxybutylamino group, a 1,2-dihydroxypentylamino group, a 1,2-dihydroxyhexylamino group, and a 1,2,3-trihydroxyhexylamino group; a branched C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups such as a 1,1′-dihydroxyisopropylamino group and a 1,1′-dihydroxypentylamino group; and the like. Among these, preferred is a group represented by the above formula (A1-7) or (A1-8).

Specific examples of a compound in which A¹ in the above formula (1) is a C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups are shown in Tables 21 to 25. However, the present invention shall not be limited to these specific examples. Abbreviations in Tables 21 to 25 have the following meanings.

SMe: sulfomethyl (*—CH₂—SO₃H)

2-SEt: 2-sulfoethyl (*—CH₂CH₂—SO₃H)

3-S^(n)Pr: 3-sulfo-n-propyl (*—CH₂CH₂CH₂—SO₃H)

4-S^(n)Bu: 3-sulfo-n-butyl (*—CH₂CH₂CH₂CH₂—SO₃H)

The symbol “*” in the above formulae indicates a position of attachment to the oxygen atom.

TABLE 21 No. Q R¹¹ R¹² A¹ 1 Cl SMe SMe Formula (A1-7) 2 Cl SMe 2-SEt Formula (A1-7) 3 Cl SMe 3-S^(n)Pr Formula (A1-7) 4 Cl SMe 4-S^(n)Bu Formula (A1-7) 5 Cl 2-SEt 2-SEt Formula (A1-7) 6 Cl 2-SEt 3-S^(n)Pr Formula (A1-7) 7 Cl 2-SEt 4-S^(n)Bu Formula (A1-7) 8 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-7) 9 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-7) 10 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-7) 11 Cl SMe SMe Formula (A1-8) 12 Cl SMe 2-SEt Formula (A1-8) 13 Cl SMe 3-S^(n)Pr Formula (A1-8) 14 Cl SMe 4-S^(n)Bu Formula (A1-8) 15 Cl 2-SEt 2-SEt Formula (A1-8) 16 Cl 2-SEt 3-S^(n)Pr Formula (A1-8) 17 Cl 2-SEt 4-S^(n)Bu Formula (A1-8) 18 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-8) 19 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-8) 20 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-8) 21 Cl SMe SMe Formula (A1-6), R^(A13) = CH(OH)CH₂(OH) 22 Cl SMe 2-SEt Formula (A1-6), R^(A13) = CH(OH)CH₂(OH) 23 Cl SMe 3-S^(n)Pr Formula (A1-6), R^(A13) = CH(OH)CH₂(OH) 24 Cl SMe 4-S^(n)Bu Formula (A1-6), R^(A13) = CH(OH)CH₂(OH) 25 Cl 2-SEt 2-SEt Formula (A1-6), R^(A13) = CH(OH)CH₂(OH) 26 Cl 2-SEt 3-S^(n)Pr Formula (A1-6), R^(A13) = CH(OH)CH₂(OH) 27 Cl 2-SEt 4-S^(n)Bu Formula (A1-6), R^(A13) = CH(OH)CH₂(OH) 28 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-6), R^(A13) = CH(OH)CH₂(OH) 29 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-6), R^(A13) = CH(OH)CH₂(OH) 30 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-6), R^(A13) = CH(OH)CH₂(OH)

TABLE 22 No. Q R¹¹ R¹² A¹ 31 Cl SMe SMe Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 32 Cl SMe 2-SEt Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 33 Cl SMe 3-S^(n)Pr Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 34 Cl SMe 4-S^(n)Bu Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 35 Cl 2-SEt 2-SEt Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 36 Cl 2-SEt 3-S^(n)Pr Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 37 Cl 2-SEt 4-S^(n)Bu Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 38 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 39 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 40 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-6), R^(A13) = CH₂CH (OH) CH₂CH₂OH 41 Cl SMe SMe Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 42 Cl SMe 2-SEt Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 43 Cl SMe 3-S^(n)Pr Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 44 Cl SMe 4-S^(n)Bu Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 45 Cl 2-SEt 2-SEt Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 46 Cl 2-SEt 3-S^(n)Pr Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 47 Cl 2-SEt 4-S^(n)Bu Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 48 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 49 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 50 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-6), R^(A13) = CH₂CH₂CH (OH) CH₂CH₂OH 51 Br SMe SMe Formula (A1-7) 52 Br SMe 2-SEt Formula (A1-7) 53 Br SMe 3-S^(n)Pr Formula (A1-7) 54 Br SMe 4-S^(n)Bu Formula (A1-7) 55 Br 2-SEt 2-SEt Formula (A1-7) 56 Br 2-SEt 3-S^(n)Pr Formula (A1-7) 57 Br 2-SEt 4-S^(n)Bu Formula (A1-7) 58 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-7) 59 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-7) 60 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-7)

TABLE 23 No. Q R¹¹ R¹² A¹ 61 Br SMe SMe Formula (A1-8) 62 Br SMe 2-SEt Formula (A1-8) 63 Br SMe 3-S^(n)Pr Formula (A1-8) 64 Br SMe 4-S^(n)Bu Formula (A1-8) 65 Br 2-SEt 2-SEt Formula (A1-8) 66 Br 2-SEt 3-S^(n)Pr Formula (A1-8) 67 Br 2-SEt 4-S^(n)Bu Formula (A1-8) 68 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-8) 69 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-8) 70 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-8) 71 Br SMe SMe Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 72 Br SMe 2-SEt Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 73 Br SMe 3-S^(n)Pr Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 74 Br SMe 4-S^(n)Bu Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 75 Br 2-SEt 2-SEt Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 76 Br 2-SEt 3-S^(n)Pr Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 77 Br 2-SEt 4-S^(n)Bu Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 78 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 79 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 80 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 81 Br SMe SMe Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 82 Br SMe 2-SEt Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 83 Br SMe 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 84 Br SMe 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 85 Br 2-SEt 2-SEt Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 86 Br 2-SEt 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 87 Br 2-SEt 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 88 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 89 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 90 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH

TABLE 24 No. Q R¹¹ R¹² A¹ 91 Br SMe SMe Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 92 Br SMe 2-SEt Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 93 Br SMe 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 94 Br SMe 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 95 Br 2-SEt 2-SEt Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 96 Br 2-SEt 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 97 Br 2-SEt 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 98 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 99 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 100 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 101 F SMe SMe Formula (A1-7) 102 F SMe 2-SEt Formula (A1-7) 103 F SMe 3-S^(n)Pr Formula (A1-7) 104 F SMe 4-S^(n)Bu Formula (A1-7) 105 F 2-SEt 2-SEt Formula (A1-7) 106 F 2-SEt 3-S^(n)Pr Formula (A1-7) 107 F 2-SEt 4-S^(n)Bu Formula (A1-7) 108 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-7) 109 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-7) 110 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-7) 111 F SMe SMe Formula (A1-8) 112 F SMe 2-SEt Formula (A1-8) 113 F SMe 3-S^(n)Pr Formula (A1-8) 114 F SMe 4-S^(n)Bu Formula (A1-8) 115 F 2-SEt 2-SEt Formula (A1-8) 116 F 2-SEt 3-S^(n)Pr Formula (A1-8) 117 F 2-SEt 4-S^(n)Bu Formula (A1-8) 118 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-8) 119 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-8) 120 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-8)

TABLE 25 No. Q R¹¹ R¹² A¹ 121 F SMe SMe Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 122 F SMe 2-SEt Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 123 F SMe 3-S^(n)Pr Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 124 F SMe 4-S^(n)Bu Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 125 F 2-SEt 2-SEt Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 126 F 2-SEt 3-S^(n)Pr Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 127 F 2-SEt 4-S^(n)Bu Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 128 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 129 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 130 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-6), RA¹³ = CH(OH)CH₂(OH) 131 F SMe SMe Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 132 F SMe 2-SEt Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 133 F SMe 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 134 F SMe 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 135 F 2-SEt 2-SEt Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 136 F 2-SEt 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 137 F 2-SEt 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 138 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 139 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 140 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH(OH)CH₂CH₂OH 141 F SMe SMe Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 142 F SMe 2-SEt Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 143 F SMe 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 144 F SMe 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 145 F 2-SEt 2-SEt Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 146 F 2-SEt 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 147 F 2-SEt 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 148 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 149 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH 150 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-6), RA¹³ = CH₂CH₂CH(OH)CH₂CH₂OH

When A¹ in the above formula (1) is a C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups, preferred compounds include, for example, one in which in the above formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a group represented by the above formula (A1-7) or (A1-8).

(Group Represented by Formula (A1-3))

In the above formula (A1-3), m represents an integer of 1 to 6, preferably an integer of 2 to 5, and more preferably 2. n represents an integer of 1 to 5, preferably an integer of 1 to 3.

Specific examples of a compound in which A¹ in the above formula (1) is a group represented by the above formula (A1-3) are shown in Tables 26 to 31 below. However, the present invention shall not be limited to these specific examples. Abbreviations in Tables 26 to 31 have the following meanings.

SMe: sulfomethyl (*—CH₂—SO₃H)

2-SEt: 2-sulfoethyl (*—CH₂CH₂—SO₃H)

3-S^(n)Pr: 3-sulfo-n-propyl (*—CH₂CH₂CH₂—SO₃H)

4-S^(n)Bu: 3-sulfo-n-butyl (*—CH₂CH₂CH₂CH₂—SO₃H)

The symbol “*” in the above formulae indicates a position of attachment to the oxygen atom.

TABLE 26 No. Q R¹¹ R¹² A¹ 1 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 1 2 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 2 3 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 3 4 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 4 5 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 5 6 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 1 7 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 2 8 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 3 9 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 4 10 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 5 11 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 1 12 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 2 13 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 3 14 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 4 15 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 5 16 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 1 17 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 2 18 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 3 19 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 4 20 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 5 21 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 1 22 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 2 23 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 3 24 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 4 25 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 5 26 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 1 27 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 2 28 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 3 29 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 4 30 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 5

TABLE 27 No. Q R¹¹ R¹² A¹ 31 Cl SMe SMe Formula (A1-3), m = 2, n = 1 32 Cl SMe SMe Formula (A1-3), m = 2, n = 2 33 Cl SMe SMe Formula (A1-3), m = 2, n = 3 34 Cl SMe 2-SEt Formula (A1-3), m = 2, n = 1 35 Cl SMe 2-SEt Formula (A1-3), m = 2, n = 2 36 Cl SMe 2-SEt Formula (A1-3), m = 2, n = 3 37 Cl SMe 3-S^(n)Pr Formula (A1-3), m = 2, n = 1 38 Cl SMe 3-S^(n)Pr Formula (A1-3), m = 2, n = 2 39 Cl SMe 3-S^(n)Pr Formula (A1-3), m = 2, n = 3 40 Cl SMe 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 41 Cl SMe 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 42 Cl SMe 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 43 Cl 2-SEt 2-SEt Formula (A1-3), m = 2, n = 1 44 Cl 2-SEt 2-SEt Formula (A1-3), m = 2, n = 2 45 Cl 2-SEt 2-SEt Formula (A1-3), m = 2, n = 3 46 Cl 2-SEt 3-S^(n)Pr Formula (A1-3), m = 2, n = 1 47 Cl 2-SEt 3-S^(n)Pr Formula (A1-3), m = 2, n = 2 48 Cl 2-SEt 3-S^(n)Pr Formula (A1-3), m = 2, n = 3 49 Cl 2-SEt 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 50 Cl 2-SEt 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 51 Cl 2-SEt 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 52 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 53 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 54 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 55 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 56 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 57 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 58 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 1 59 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 2 60 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 3

TABLE 28 No. Q R¹¹ R¹² A¹ 61 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 4 62 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 5 63 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 1 64 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 2 65 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 3 66 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 4 67 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 5 68 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 1 69 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 2 70 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 3 71 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 4 72 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 5 73 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 1 74 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 2 75 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 3 76 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 4 77 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 5 78 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 1 79 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 2 80 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 3 81 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 4 82 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 5 83 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 1 84 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 2 85 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 3 86 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 4 87 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 5 88 Br SMe SMe Formula (A1-3), m = 2, n = 1 89 Br SMe SMe Formula (A1-3), m = 2, n = 2 90 Br SMe SMe Formula (A1-3), m = 2, n = 3

TABLE 29 No. Q R¹¹ R¹² A¹ 91 Br SMe 2-SEt Formula (A1-3), m = 2, n = 1 92 Br SMe 2-SEt Formula (A1-3), m = 2, n = 2 93 Br SMe 2-SEt Formula (A1-3), m = 2, n = 3 94 Br SMe 3-S^(n)Pr Formula (A1-3), m = 2, n = 1 95 Br SMe 3-S^(n)Pr Formula (A1-3), m = 2, n = 2 96 Br SMe 3-S^(n)Pr Formula (A1-3), m = 2, n = 3 97 Br SMe 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 98 Br SMe 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 99 Br SMe 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 100 Br 2-SEt 2-SEt Formula (A1-3), m = 2, n = 1 101 Br 2-SEt 2-SEt Formula (A1-3), m = 2, n = 2 102 Br 2-SEt 2-SEt Formula (A1-3), m = 2, n = 3 103 Br 2-SEt 3-S^(n)Pr Formula (A1-3), m = 2, n = 1 104 Br 2-SEt 3-S^(n)Pr Formula (A1-3), m = 2, n = 2 105 Br 2-SEt 3-S^(n)Pr Formula (A1-3), m = 2, n = 3 106 Br 2-SEt 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 107 Br 2-SEt 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 108 Br 2-SEt 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 109 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 110 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 111 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 112 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 113 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 114 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 115 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 1 116 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 2 117 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 3 118 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 4 119 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 1, n = 5 120 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 1

TABLE 30 No. Q R¹¹ R¹² A¹ 121 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 2 122 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 3 123 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 4 124 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 2, n = 5 125 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 1 126 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 2 127 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 3 128 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 4 129 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 3, n = 5 130 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 1 131 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 2 132 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 3 133 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 4 134 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 4, n = 5 135 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 1 136 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 2 137 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 3 138 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 4 139 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 5, n = 5 140 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 1 141 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 2 142 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 3 143 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 4 144 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-3), m = 6, n = 5 145 F SMe SMe Formula (A1-3), m = 2, n = 1 146 F SMe SMe Formula (A1-3), m = 2, n = 2 147 F SMe SMe Formula (A1-3), m = 2, n = 3 148 F SMe 2-SEt Formula (A1-3), m = 2, n = 1 149 F SMe 2-SEt Formula (A1-3), m = 2, n = 2 150 F SMe 2-SEt Formula (A1-3), m = 2, n = 3

TABLE 31 No. Q R¹¹ R¹² A¹ 151 F SMe 3-S^(n)Pr Formula (A1-3), m = 2, n = 1 152 F SMe 3-S^(n)Pr Formula (A1-3), m = 2, n = 2 153 F SMe 3-S^(n)Pr Formula (A1-3), m = 2, n = 3 154 F SMe 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 155 F SMe 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 156 F SMe 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 157 F 2-SEt 2-SEt Formula (A1-3), m = 2, n = 1 158 F 2-SEt 2-SEt Formula (A1-3), m = 2, n = 2 159 F 2-SEt 2-SEt Formula (A1-3), m = 2, n = 3 160 F 2-SEt 3-S^(n)Pr Formula (A1-3), m = 2, n = 1 161 F 2-SEt 3-S^(n)Pr Formula (A1-3), m = 2, n = 2 162 F 2-SEt 3-S^(n)Pr Formula (A1-3), m = 2, n = 3 163 F 2-SEt 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 164 F 2-SEt 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 165 F 2-SEt 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 166 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 167 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 168 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-3), m = 2, n = 3 169 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-3), m = 2, n = 1 170 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-3), m = 2, n = 2 171 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-3), m = 2, n = 3

When A¹ in the above formula (1) is a group represented by the above formula (A1-3), preferred compounds include, for example, one represented by the above formula (1-17) or (1-18).

(Group Represented by Formula (A1-4))

In the above formula (A1-4), n represents an integer of 2 to 6, preferably 3.

Specific examples of a compound in which A¹ in the above formula (1) is a group represented by the above formula (A1-4) are shown in Tables 32 to 37 below. However, the present invention shall not be limited to these specific examples. Abbreviations in Tables 32 to 37 have the following meanings.

SMe: sulfomethyl (*—CH₂—SO₃H)

2-SEt: 2-sulfoethyl (*—CH₂CH₂—SO₃H)

3-S^(n)Pr: 3-sulfo-n-propyl (*—CH₂CH₂CH₂—SO₃H)

4-S^(n)Bu: 3-sulfo-n-butyl (*—CH₂CH₂CH₂CH₂—SO₃H)

The symbol “*” in the above formulae indicates a position of attachment to the oxygen atom.

TABLE 32 No. Q R¹¹ R¹² A¹ 1 Cl SMe SMe Formula (A1-4), n = 1 2 Cl SMe 2-SEt Formula (A1-4), n = 1 3 Cl SMe 3-S^(n)Pr Formula (A1-4), n = 1 4 Cl SMe 4-S^(n)Bu Formula (A1-4), n = 1 5 Cl 2-SEt 2-SEt Formula (A1-4), n = 1 6 Cl 2-SEt 3-S^(n)Pr Formula (A1-4), n = 1 7 Cl 2-SEt 4-S^(n)Bu Formula (A1-4), n = 1 8 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 1 9 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 1 10 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 1 11 Cl SMe SMe Formula (A1-4), n = 2 12 Cl SMe 2-SEt Formula (A1-4), n = 2 13 Cl SMe 3-S^(n)Pr Formula (A1-4), n = 2 14 Cl SMe 4-S^(n)Bu Formula (A1-4), n = 2 15 Cl 2-SEt 2-SEt Formula (A1-4), n = 2 16 Cl 2-SEt 3-S^(n)Pr Formula (A1-4), n = 2 17 Cl 2-SEt 4-S^(n)Bu Formula (A1-4), n = 2 18 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 2 19 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 2 20 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 2 21 Cl SMe SMe Formula (A1-4), n = 3 22 Cl SMe 2-SEt Formula (A1-4), n = 3 23 Cl SMe 3-S^(n)Pr Formula (A1-4), n = 3 24 Cl SMe 4-S^(n)Bu Formula (A1-4), n = 3 25 Cl 2-SEt 2-SEt Formula (A1-4), n = 3 26 Cl 2-SEt 3-S^(n)Pr Formula (A1-4), n = 3 27 Cl 2-SEt 4-S^(n)Bu Formula (A1-4), n = 3 28 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 3 29 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 3 30 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 3

TABLE 33 No. Q R¹¹ R¹² A¹ 31 Cl SMe SMe Formula (A1-4), n = 4 32 Cl SMe 2-SEt Formula (A1-4), n = 4 33 Cl SMe 3-S^(n)Pr Formula (A1-4), n = 4 34 Cl SMe 4-S^(n)Bu Formula (A1-4), n = 4 35 Cl 2-SEt 2-SEt Formula (A1-4), n = 4 36 Cl 2-SEt 3-S^(n)Pr Formula (A1-4), n = 4 37 Cl 2-SEt 4-S^(n)Bu Formula (A1-4), n = 4 38 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 4 39 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 4 40 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 4 41 Cl SMe SMe Formula (A1-4), n = 5 42 Cl SMe 2-SEt Formula (A1-4), n = 5 43 Cl SMe 3-S^(n)Pr Formula (A1-4), n = 5 44 Cl SMe 4-S^(n)Bu Formula (A1-4), n = 5 45 Cl 2-SEt 2-SEt Formula (A1-4), n = 5 46 Cl 2-SEt 3-S^(n)Pr Formula (A1-4), n = 5 47 Cl 2-SEt 4-S^(n)Bu Formula (A1-4), n = 5 48 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 5 49 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 5 50 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 5 51 Cl SMe SMe Formula (A1-4), n = 6 52 Cl SMe 2-SEt Formula (A1-4), n = 6 53 Cl SMe 3-S^(n)Pr Formula (A1-4), n = 6 54 Cl SMe 4-S^(n)Bu Formula (A1-4), n = 6 55 Cl 2-SEt 2-SEt Formula (A1-4), n = 6 56 Cl 2-SEt 3-S^(n)Pr Formula (A1-4), n = 6 57 Cl 2-SEt 4-S^(n)Bu Formula (A1-4), n = 6 58 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 6 59 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 6 60 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 6

TABLE 34 No. Q R¹¹ R¹² A¹ 61 Br SMe SMe Formula (A1-4), n = 1 62 Br SMe 2-SEt Formula (A1-4), n = 1 63 Br SMe 3-S^(n)Pr Formula (A1-4), n = 1 64 Br SMe 4-S^(n)Bu Formula (A1-4), n = 1 65 Br 2-SEt 2-SEt Formula (A1-4), n = 1 66 Br 2-SEt 3-S^(n)Pr Formula (A1-4), n = 1 67 Br 2-SEt 4-S^(n)Bu Formula (A1-4), n = 1 68 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 1 69 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 1 70 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 1 71 Br SMe SMe Formula (A1-4), n = 2 72 Br SMe 2-SEt Formula (A1-4), n = 2 73 Br SMe 3-S^(n)Pr Formula (A1-4), n = 2 74 Br SMe 4-S^(n)Bu Formula (A1-4), n = 2 75 Br 2-SEt 2-SEt Formula (A1-4), n = 2 76 Br 2-SEt 3-S^(n)Pr Formula (A1-4), n = 2 77 Br 2-SEt 4-S^(n)Bu Formula (A1-4), n = 2 78 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 2 79 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 2 80 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 2 81 Br SMe SMe Formula (A1-4), n = 3 82 Br SMe 2-SEt Formula (A1-4), n = 3 83 Br SMe 3-S^(n)Pr Formula (A1-4), n = 3 84 Br SMe 4-S^(n)Bu Formula (A1-4), n = 3 85 Br 2-SEt 2-SEt Formula (A1-4), n = 3 86 Br 2-SEt 3-S^(n)Pr Formula (A1-4), n = 3 87 Br 2-SEt 4-S^(n)Bu Formula (A1-4), n = 3 88 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 3 89 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 3 90 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 3

TABLE 35 No. Q R¹¹ R¹² A¹ 91 Br SMe SMe Formula (A1-4), n = 4 92 Br SMe 2-SEt Formula (A1-4), n = 4 93 Br SMe 3-S^(n)Pr Formula (A1-4), n = 4 94 Br SMe 4-S^(n)Bu Formula (A1-4), n = 4 95 Br 2-SEt 2-SEt Formula (A1-4), n = 4 96 Br 2-SEt 3-S^(n)Pr Formula (A1-4), n = 4 97 Br 2-SEt 4-S^(n)Bu Formula (A1-4), n = 4 98 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 4 99 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 4 100 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 4 101 Br SMe SMe Formula (A1-4), n = 5 102 Br SMe 2-SEt Formula (A1-4), n = 5 103 Br SMe 3-S^(n)Pr Formula (A1-4), n = 5 104 Br SMe 4-S^(n)Bu Formula (A1-4), n = 5 105 Br 2-SEt 2-SEt Formula (A1-4), n = 5 106 Br 2-SEt 3-S^(n)Pr Formula (A1-4), n = 5 107 Br 2-SEt 4-S^(n)Bu Formula (A1-4), n = 5 108 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 5 109 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 5 110 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 5 111 Br SMe SMe Formula (A1-4), n = 6 112 Br SMe 2-SEt Formula (A1-4), n = 6 113 Br SMe 3-S^(n)Pr Formula (A1-4), n = 6 114 Br SMe 4-S^(n)Bu Formula (A1-4), n = 6 115 Br 2-SEt 2-SEt Formula (A1-4), n = 6 116 Br 2-SEt 3-S^(n)Pr Formula (A1-4), n = 6 117 Br 2-SEt 4-S^(n)Bu Formula (A1-4), n = 6 118 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 6 119 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 6 120 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 6

TABLE 36 No. Q R¹¹ R¹² A¹ 121 F SMe SMe Formula (A1-4), n = 1 122 F SMe 2-SEt Formula (A1-4), n = 1 123 F SMe 3-S^(n)Pr Formula (A1-4), n = 1 124 F SMe 4-S^(n)Bu Formula (A1-4), n = 1 125 F 2-SEt 2-SEt Formula (A1-4), n = 1 126 F 2-SEt 3-S^(n)Pr Formula (A1-4), n = 1 127 F 2-SEt 4-S^(n)Bu Formula (A1-4), n = 1 128 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 1 129 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 1 130 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 1 131 F SMe SMe Formula (A1-4), n = 2 132 F SMe 2-SEt Formula (A1-4), n = 2 133 F SMe 3-S^(n)Pr Formula (A1-4), n = 2 134 F SMe 4-S^(n)Bu Formula (A1-4), n = 2 135 F 2-SEt 2-SEt Formula (A1-4), n = 2 136 F 2-SEt 3-S^(n)Pr Formula (A1-4), n = 2 137 F 2-SEt 4-S^(n)Bu Formula (A1-4), n = 2 138 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 2 139 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 2 140 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 2 141 F SMe SMe Formula (A1-4), n = 3 142 F SMe 2-SEt Formula (A1-4), n = 3 143 F SMe 3-S^(n)Pr Formula (A1-4), n = 3 144 F SMe 4-S^(n)Bu Formula (A1-4), n = 3 145 F 2-SEt 2-SEt Formula (A1-4), n = 3 146 F 2-SEt 3-S^(n)Pr Formula (A1-4), n = 3 147 F 2-SEt 4-S^(n)Bu Formula (A1-4), n = 3 148 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 3 149 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 3 150 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 3

TABLE 37 No. Q R¹¹ R¹² A¹ 151 F SMe SMe Formula (A1-4), n = 4 152 F SMe 2-SEt Formula (A1-4), n = 4 153 F SMe 3-S^(n)Pr Formula (A1-4), n = 4 154 F SMe 4-S^(n)Bu Formula (A1-4), n = 4 155 F 2-SEt 2-SEt Formula (A1-4), n = 4 156 F 2-SEt 3-S^(n)Pr Formula (A1-4), n = 4 157 F 2-SEt 4-S^(n)Bu Formula (A1-4), n = 4 158 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 4 159 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 4 160 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 4 161 F SMe SMe Formula (A1-4), n = 5 162 F SMe 2-SEt Formula (A1-4), n = 5 163 F SMe 3-S^(n)Pr Formula (A1-4), n = 5 164 F SMe 4-S^(n)Bu Formula (A1-4), n = 5 165 F 2-SEt 2-SEt Formula (A1-4), n = 5 166 F 2-SEt 3-S^(n)Pr Formula (A1-4), n = 5 167 F 2-SEt 4-S^(n)Bu Formula (A1-4), n = 5 168 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 5 169 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 5 170 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 5 171 F SMe SMe Formula (A1-4), n = 6 172 F SMe 2-SEt Formula (A1-4), n = 6 173 F SMe 3-S^(n)Pr Formula (A1-4), n = 6 174 F SMe 4-S^(n)Bu Formula (A1-4), n = 6 175 F 2-SEt 2-SEt Formula (A1-4), n = 6 176 F 2-SEt 3-S^(n)Pr Formula (A1-4), n = 6 177 F 2-SEt 4-S^(n)Bu Formula (A1-4), n = 6 178 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-4), n = 6 179 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-4), n = 6 180 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-4), n = 6

When A¹ in the above formula (1) is a group represented by an above formula (A1-4), preferred compounds include, for example, one in which in the above formula (1-1), Q is a chlorine atom, x is 3, and A¹ is represented by the above formula (A1-4) wherein n is 3.

(Cyclic Amine Group)

As a cyclic amine group, preferred is a 3- to 5-membered ring group having one nitrogen atom as a ring atom. More preferred is a 5-membered ring group having one nitrogen atom. Examples of the 3- to 5-membered ring having one nitrogen atom include an aziridine ring, an azetidine ring, a pyrrolidine ring and the like. Among cyclic amine groups, preferred is one represented by the above formula (A1-9).

In the above formula (A1-9), each R^(A14) to R^(A21) independently represents a hydrogen atom or a substituent. There is no particular limitation for the substituent, but examples include a hydroxy group, a substituted or unsubstituted C1-C4 alkyl group, a halogen atom, a sulfo group, a carboxy group, a phospho group, a substituted or unsubstituted amino group, a nitro group, a cyano group, an alkoxy group, a phenyl group, a naphthyl group and the like.

C1-C4 alkyl groups include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, a t-butyl group and the like. There is no particular limitation for a substituent that may be present in a C1-C4 alkyl group, but examples include a halogen atom, a sulfo group, a carboxy group, a phospho group, a substituted or unsubstituted amino group, a nitro group, a cyano group, an alkoxy group, a phenyl group, a naphthyl group and the like.

Halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Substituted amino groups include, for example, a mono-(C1-C4 alkyl)amino group, a dimethylamino group, an ethylmethylamino group and the like.

Alkoxy groups include, for example, C1-C4 alkoxy groups such as a methoxy group, an ethoxy group, and a propoxy group.

In the above formula (A1-9), each R^(A14) to R^(A21) is preferably a hydrogen atom.

Specific examples of a compound in which A¹ in the above formula (1) is a cyclic amine group are shown in Tables 38 and 39 below. However, the present invention shall not be limited to these specific examples. Abbreviations in Tables 38 and 39 have the following meanings.

SMe: sulfomethyl (*—CH₂—SO₃H)

2-SEt: 2-sulfoethyl (*—CH₂CH₂—SO₃H)

3-S^(n)Pr: 3-sulfo-n-propyl (*—CH₂CH₂CH₂—SO₃H)

4-S^(n)Bu: 3-sulfo-n-butyl (*—CH₂CH₂CH₂CH₂—SO₃H)

The symbol “*” in the above formulae indicates a position of attachment to the oxygen atom.

TABLE 38 No. Q R¹¹ R¹² A¹  1 Cl SMe SMe Formula (A1-9), R^(A14)-R^(A21) = H  2 Cl SMe 2-SEt Formula (A1-9), R^(A14)-R^(A21) = H  3 Cl SMe 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H  4 Cl SMe 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H  5 Cl 2-SEt 2-SEt Formula (A1-9), R^(A14)-R^(A21) = H  6 Cl 2-SEt 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H  7 Cl 2-SEt 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H  8 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H  9 Cl 3-S^(n)Pr 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 10 Cl 4-S^(n)Bu 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 11 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = Cl 12 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = CH₃ 13 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14), R^(A16), R^(A18), R^(A20) = H, R^(A15), R^(A17), R^(A19), R^(A21) = Cl 14 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14) = OH, R^(A15)-R^(A21) = H 15 Cl 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14) = CH₂OH, R^(A15)-R^(A21) = H 16 Br SMe SMe Formula (A1-9), R^(A14)-R^(A21) = H 17 Br SMe 2-SEt Formula (A1-9), R^(A14)-R^(A21) = H 18 Br SMe 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H 19 Br SMe 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 20 Br 2-SEt 2-SEt Formula (A1-9), R^(A14)-R^(A21) = H 21 Br 2-SEt 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H 22 Br 2-SEt 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 23 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H 24 Br 3-S^(n)Pr 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 25 Br 4-S^(n)Bu 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 26 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H 27 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = CH₃ 28 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14), R^(A16), R^(A18), R^(A20) = H, R^(A15), R^(A17), R^(A19), R^(A21) = Cl 29 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14) = OH, R^(A15)-R^(A21) = H 30 Br 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14) = CH₂OH, R^(A15)-R^(A21) = H

TABLE 39 No. Q R¹¹ R¹² A¹ 31 F SMe SMe Formula (A1-9), R^(A14)-R^(A21) = H 32 F SMe 2-SEt Formula (A1-9), R^(A14)-R^(A21) = H 33 F SMe 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H 34 F SMe 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 35 F 2-SEt 2-SEt Formula (A1-9), R^(A14)-R^(A21) = H 36 F 2-SEt 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H 37 F 2-SEt 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 38 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = H 39 F 3-S^(n)Pr 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 40 F 4-S^(n)Bu 4-S^(n)Bu Formula (A1-9), R^(A14)-R^(A21) = H 41 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = Cl 42 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14)-R^(A21) = CH₃ 43 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14), R^(A16), R^(A18), R^(A20) = H, R^(A15), R^(A17), R^(A19), R^(A21) = Cl 44 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14) = OH, R^(A15)-R^(A21) = H 45 F 3-S^(n)Pr 3-S^(n)Pr Formula (A1-9), R^(A14) = CH₂OH, R^(A15)-R^(A21) = H

When A¹ in the above formula (1) is a cyclic amine group, preferred compounds include, for example, one in which in the above formula (1-1), Q is a chlorine atom, x is 3, and A¹ is a group represented by the above formula (A1-9), and R^(A14) to R^(A21) in the above formula (A1-9) are each a hydrogen atom.

With regard to all components and items, combinations of those preferred are more preferred, and combinations of those more preferred are even more preferred. The same applies to combinations of those preferred and those more preferred and the like.

The compound represented by the above formula (1) can be manufactured as follows. It should be noted that Q, x, R¹¹, and R¹², which are appropriately used in the following formulae (10-1) to (14), each have the same meaning as defined in the formula (1).

First, a compound represented by the following formula (10-1) obtained in accordance with the method described in Japanese Unexamined Patent Application Publication No. 2004-75719 by using 2-amino-4-halogenophenol as a raw material is converted into a methyl-ω-sulfonic acid derivative represented by the following formula (11) using sodium bisulfite and formalin. Then, the resulting methyl-ω-sulfonic acid derivative represented by the following formula (11) and a compound represented by the following formula (12) diazotized according to the conventional method are subjected to a coupling reaction at a reaction temperature of 0 to 15° C. and at pH 4 to 6. Subsequently, a hydrolysis reaction is performed at a reaction temperature of 80 to 95° C. and at pH 10.5 to 11.5 to obtain a compound represented by the following formula (13-1). Moreover, a compound represented by the following formula (13-2) is obtained as described above except that a compound represented by the following formula (10-2) is used instead of the compound represented by the following formula (10-1).

Subsequently, the compound (1 equivalent) represented by the above formula (13-1), the compound (1 equivalent) represented by the above formula (13-2), and a cyanuric halide (such as cyanuric chloride, 1 equivalent) are condensed at a reaction temperature of 15 to 45° C. and at pH 5 to 8 to obtain a compound represented by the following formula (14). It should be noted that one of the compounds (1 equivalent) represented by the above formula (13-1) and the compound (1 equivalent) represented by the above formula (13-2) may be reacted with a cyanuric halide (1 equivalent), and then the resulting reaction product may further be reacted with the other compound.

Subsequently, the compound represented by the above formula (14) and a compound represented by a formula H-A¹ are reacted at a reaction temperature of 55 to 95° C. and at pH 6 to 9 to cause a de-HCl reaction. This can lead to production of the compound represented by the above formula (1).

[Compound Represented by Formula (2)]

In the above formula (2), each Q²¹ to Q²⁴ independently represents a halogen atom. Halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom or a chlorine atom is preferred, and a chlorine atom is more preferred.

In the above formula (2), each R²¹ to R²⁴ independently represents an alkyl group substituted with an ionic hydrophilic group. The carbon number of an alkyl group moiety is usually 1 to 4, preferably 1 to 3, and more preferably 3. Ionic hydrophilic groups include a group selected from a sulfo group, a carboxy group, a phospho group, and a quaternary ammonium group. Among these, preferred is a group selected from a sulfo group, a carboxy group, and a phospho group. More preferred is a group selected from a sulfo group and a carboxy group. Even more preferred is a sulfo group. There is no particular limitation for the number of substitutions in an ionic hydrophilic group, but it is usually 1 to 5, preferably 1 to 4, more preferably 1 to 3, even more preferably 1 or 2, and in particular preferably 1.

Specific examples of an alkyl group substituted with an ionic hydrophilic group include, for example, a sulfomethyl group, a sulfoethyl group, a 2,3-disulfopropyl group, a 3-sulfopropyl group, a 4-sulfobutyl group, a 5-sulfopentyl group, a 6-sulfohexyl group, a 7-sulfoheptyl group, an 8-sulfooctyl group, a carboxymethyl group, a carboxyethyl group, a 3-carboxypropyl group, a 4-carboxybutyl group, a 5-carboxypentyl group, a 6-carboxyhexyl group, a 7-carboxyheptyl group, an 8-carboxyoctyl group, a phosphomethyl group, a phosphoethyl group, a 3-phosphopropyl group, a 4-phosphobutyl group, a 5-phosphopentyl group, a 6-phosphohexyl group, a 7-phosphoheptyl group, an 8-phosphooctyl group, a trimethylammoniummethyl group, a trimethylammoniumethyl group, a 3-trimethylammoniumpropyl group, a 4-trimethylammoniumbutyl group, a 5-trimethylammoniumpentyl group, a 6-trimethylammoniumhexyl group, a 7-trimethylammoniumheptyl group, an 8-trimethylammoniumoctyl group, a 2-methyl-3-sulfopropyl group, a 2,2-dimethyl-3-sulfopropyl group, a 4-sulfocyclohexyl group, a 2,5-disulfocyclohexylmethyl group and the like. Preferred is a 3-sulfopropyl group.

In the above formula (2), A² represents a divalent group. Divalent groups include, for example, an alkylenediamino group, a nitrogen-containing heterocyclic group, an arylenediamino group, an aminoalkylthio group, and an aminoarylthio group. Among these, preferred are an alkylenediamino group and a nitrogen-containing heterocyclic group. More preferred is a nitrogen-containing heterocyclic group.

Alkylenediamino groups include a group having a linear, branched, or cyclic alkylene moiety. The alkylene moiety is preferably linear or branched, more preferably linear. The carbon number of the alkylene moiety is usually 2 to 12, preferably 2 to 8, more preferably 2 to 6, and even more preferably 2 to 4. Specific examples of the alkylenediamino group include, for example, 1,2-ethylenediamino, 1,2-propylenediamino, 1,3-propylenediamino, 1,2-butylenediamino, 1,4-butylenediamino, 1,2-pentylenediamino, 1,5-pentylenediamino, 1,2-hexylenediamino, 1,6-hexylenediamino, 2-methyl-1,3-propylenediamino, 1,2-cyclopentylenediamino, 1,2-cyclohexylenediamine, 1,4-piperazinyl and the like. Among these, 1,4-piperazinyl is preferred.

Nitrogen-containing heterocyclic groups include a nitrogen-containing heterocyclic group of a 4- to 9-membered ring (preferably a 5- to 7-membered ring, more preferably a 5- or 6-membered ring, and even more preferably a 6-membered ring) having two nitrogen atoms as ring atoms. Specific examples of the nitrogen-containing heterocyclic group include, for example, 1,2-diazetidine, pyrazolidine, hexahydropyridazine, hexahydropyrimidine, piperazine, 1,2-diazepane, 1,3-diazepane, 1,4-diazepane, 1,2-diazocane, 1,4-diazocane, and 1,4-diazonane. Among these, piperazine (in particular 1,4-piperazinediyl) is preferred.

Arylenediamino groups include an arylenediamino group usually having 6 to 14 carbon atoms, preferably 6 to 10 carbon atoms, and more preferably 6 carbon atoms. Specific examples of the arylenediamino group include, for example, 1,2-phenylenediamino, 1,3-phenylenediamino, 1,4-phenylenediamino, 1,8-naphthylenediamino, 2,8-naphthylenediamino and the like.

Aminoalkylthio groups include a group having a linear, branched, or cyclic alkyl moiety. The carbon number of the alkyl moiety is usually 2 to 12, preferably 2 to 8, more preferably 2 to 6, and even more preferably 2 to 4. Specific examples of the aminoalkylthio group include, for example, aminoethylthio, aminopropylthio, aminobutylthio, aminopentylthio, aminohexylthio, 3-amino-2-methylpropane-1-thio, 2-aminocyclohexane-1-thio and the like.

Aminoarylthio groups include an aminoarylthio group usually having 6 to 14 carbon atoms, preferably 6 to 10 carbon atoms, more preferably 6 carbon atoms. Specific examples of the aminoarylthio group include, for example, 2-aminophenylthio, 4-aminophenylthio, 8-aminonaphthyl-2-thio and the like.

Further, A² may usually have 1 to 5 substituents, preferably 1 to 4 substituents, more preferably 1 to 3 substituents, even more preferably 1 or 2 substituents, and in particular preferably 1 substituent. There is no particular limitation for the substituents, but examples include a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, an aryloxy group, a silyloxy group, and a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl- or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, an alkyl- or arylsulfinyl group, an alkyl- or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group and the like.

A preferred compound among the compounds represented by the above formula (2) is one represented by the above formula (2-1). In the above formula (2-1), Q²¹ to Q²⁴ and A² have the same meanings as defined in the above formula (2), including those preferred and the like. In the above formula (2-1), each x independently represents an integer of 2 to 4, and preferably 3.

Specific examples of the compound represented by the above formula (2) are shown in Tables 40 to 46 below. However, the present invention shall not be limited to these specific examples. Abbreviations in Tables 40 to 46 have the following meanings.

SMe: sulfomethyl (*—CH₂—SO₃H)

2-SEt: 2-sulfoethyl (*—CH₂CH₂—SO₃H)

3-S^(n)Pr: 3-sulfo-n-propyl (*—CH₂CH₂CH₂—SO₃H)

4-S^(n)Bu: 3-sulfo-n-butyl (*—CH₂CH₂CH₂CH₂—SO₃H)

The symbol “*” in the above formulae indicates a position of attachment to the oxygen atom.

Further, the formulae (A2-1) to (A2-5) indicated in the “A²” columns in Tables 40 to 46 are represented by the following formulae, respectively. The symbol “*” in the following formulae indicates a position of attachment to the triazine ring.

TABLE 40 No. Q²¹ Q²² Q²³ Q²⁴ R²¹ R²² R²³ R²⁴ A²  1 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-1) n = 2, Z = NH  2 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-1) n = 2, Z = NH  3 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-1) n = 2, Z = NH  4 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-1) n = 2, Z = NH  5 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-1) n = 2, Z = NH  6 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-1) n = 2, Z = NH  7 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-1) n = 2, Z = NH  8 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-1) n = 2, Z = NH  9 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-1) n = 2, Z = NH 10 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-1) n = 2, Z = NH 11 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-1), n = 2, Z = S 12 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-1), n = 2, Z = S 13 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-1), n = 2, Z = S 14 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-1), n = 2, Z = S 15 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-1), n = 2, Z = S 16 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-1), n = 2, Z = S 17 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-1), n = 2, Z = S 18 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-1), n = 2, Z = S 19 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-1), n = 2, Z = S 20 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-1), n = 2, Z = S 21 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-1), n = 3, Z = NH 22 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-1), n = 3, Z = NH 23 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-1) n = 3, Z = NH 24 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-1) n = 3, Z = NH 25 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-1) n = 3, Z = NH 26 Cl Cl Cl Cl 2-SEt 3-S^(n)pr 2-SEt 3-S^(n)Pr Formula (A2-1) n = 3, Z = NH 27 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-1) n = 3, Z = NH 28 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-1) n = 3, Z = NH 29 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-1) n = 3, Z = NH 30 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-1) n = 3, Z = NH

TABLE 41 No. Q²¹ Q²² Q²³ Q²⁴ R²¹ R²² R²³ R²⁴ A² 31 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-1) n = 3, Z = S 32 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-1) n = 3, Z = S 33 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-1) n = 3, Z = S 34 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-1) n = 3, Z = S 35 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-1) n = 3, Z = S 36 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-1) n = 3, Z = S 37 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-1) n = 3, Z = S 38 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-1) n = 3, Z = S 39 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-1) n = 3, Z = S 40 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-1) n = 3, Z = S 41 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-2) 42 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-2) 43 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-2) 44 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-2) 45 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-2) 46 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-2) 47 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-2) 48 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-2) 49 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-2) 50 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-2) 51 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-3), Z = NH 52 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-3), Z = NH 53 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-3), Z = NH 54 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-3), Z = NH 55 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-3), Z = NH 56 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-3), Z = NH 57 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-3), Z = NH 58 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-3), Z = NH 59 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-3), Z = NH 60 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-3), Z = NH

TABLE 42 No. Q²¹ Q²² Q²³ Q²⁴ R²¹ R²² R²³ R²⁴ A² 61 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-3), Z = S 62 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-3), Z = S 63 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-3), Z = S 64 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-3), Z = S 65 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-3), Z = S 66 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-3), Z = S 67 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-3), Z = S 68 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-3), Z = S 69 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-3), Z = S 70 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-3), Z = S 71 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-4), Z = NH 72 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-4), Z = NH 73 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-4), Z = NH 74 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-4), Z = NH 75 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-4), Z = NH 76 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-4), Z = NH 77 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-4), Z = NH 78 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-4), Z = NH 79 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-4), Z = NH 80 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-4), Z = NH 81 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-4), Z = S 82 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-4), Z = S 83 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-4), Z = S 84 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-4), Z = S 85 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-4), Z = S 86 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-4), Z = S 87 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-4), Z = S 88 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-4), Z = S 89 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-4), Z = S 90 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-4), Z = S

TABLE 43 No. Q²¹ Q²² Q²³ Q²⁴ R²¹ R²² R²³ R²⁴ A²  91 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-5), Z = NH  92 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-5), Z = NH  93 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-5), Z = NH  94 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-5), Z = NH  95 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-5), Z = NH  96 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-5), Z = NH  97 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-5), Z = NH  98 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-5), Z = NH  99 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-5), Z = NH 100 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-5), Z = NH 101 Cl Cl Cl Cl SMe SMe SMe SMe Formula (A2-5), Z = S 102 Cl Cl Cl Cl SMe 2-SEt SMe 2-SEt Formula (A2-5), Z = S 103 Cl Cl Cl Cl SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-5), Z = S 104 Cl Cl Cl Cl SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-5), Z = S 105 Cl Cl Cl Cl 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-5), Z = S 106 Cl Cl Cl Cl 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-5), Z = S 107 Cl Cl Cl Cl 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-5), Z = S 108 Cl Cl Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-5), Z = S 109 Cl Cl Cl Cl 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-5), Z = S 110 Cl Cl Cl Cl 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-5), Z = S 111 Cl Cl F F SMe SMe SMe SMe Formula (A2-2) 112 Cl Cl F F SMe 2-SEt SMe 2-SEt Formula (A2-2) 113 Cl Cl F F SMe 3-S'Pr SMe 3-S^(n)Pr Formula (A2-2) 114 Cl Cl F F SMe 4-S'Bu SMe 4-S^(n)Bu Formula (A2-2) 115 Cl Cl F F 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-2) 116 Cl Cl F F 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-2) 117 Cl Cl F F 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-2) 118 Cl Cl F F 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-2) 119 Cl Cl F F 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-2) 120 Cl Cl F F 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-2)

TABLE 44 No. Q²¹ Q²² Q²³ Q²⁴ R²¹ R²² R²³ R²⁴ A² 121 Cl F Cl F SMe SMe SMe SMe Formula (A2-2) 122 Cl F Cl F SMe 2-SEt SMe 2-SEt Formula (A2-2) 123 Cl F Cl F SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-2) 124 Cl F Cl F SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-2) 125 Cl F Cl F 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-2) 126 Cl F Cl F 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-2) 127 Cl F Cl F 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-2) 128 Cl F Cl F 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-2) 129 Cl F Cl F 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-2) 130 Cl F Cl F 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-2) 131 Cl Cl Br Br SMe SMe SMe SMe Formula (A2-2) 132 Cl Cl Br Br SMe 2-SEt SMe 2-SEt Formula (A2-2) 133 Cl Cl Br Br SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-2) 134 Cl Cl Br Br SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-2) 135 Cl Cl Br Br 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-2) 136 Cl Cl Br Br 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-2) 137 Cl Cl Br Br 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-2) 138 Cl Cl Br Br 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-2) 139 Cl Cl Br Br 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-2) 140 Cl Cl Br Br 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-2) 141 Cl Br Cl Br SMe SMe SMe SMe Formula (A2-2) 142 Cl Br Cl Br SMe 2-SEt SMe 2-SEt Formula (A2-2) 143 Cl Br Cl Br SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-2) 144 Cl Br Cl Br SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-2) 145 Cl Br Cl Br 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-2) 146 Cl Br Cl Br 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-2) 147 Cl Br Cl Br 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-2) 148 Cl Br Cl Br 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-2) 149 Cl Br Cl Br 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-2) 150 Cl Br Cl Br 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-2)

TABLE 45 No. Q²¹ Q²² Q²³ Q²⁴ R²¹ R²² R²³ R²⁴ A² 151 F F Br Br SMe SMe SMe SMe Formula (A2-2) 152 F F Br Br SMe 2-SEt SMe 2-SEt Formula (A2-2) 153 F F Br Br SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-2) 154 F F Br Br SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-2) 155 F F Br Br 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-2) 156 F F Br Br 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-2) 157 F F Br Br 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-2) 158 F F Br Br 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-2) 159 F F Br Br 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-2) 160 F F Br Br 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-2) 161 F Br F Br SMe SMe SMe SMe Formula (A2-2) 162 F Br F Br SMe 2-SEt SMe 2-SEt Formula (A2-2) 163 F Br F Br SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-2) 164 F Br F Br SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-2) 165 F Br F Br 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-2) 166 F Br F Br 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-2) 167 F Br F Br 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-2) 168 F Br F Br 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-2) 169 F Br F Br 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-2) 170 F Br F Br 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-2) 171 F F F F SMe SMe SMe SMe Formula (A2-2) 172 F F F F SMe 2-SEt SMe 2-SEt Formula (A2-2) 173 F F F F SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-2) 174 F F F F SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-2) 175 F F F F 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-2) 176 F F F F 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-2) 177 F F F F 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-2) 178 F F F F 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-2) 179 F F F F 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-2) 180 F F F F 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-2)

TABLE 46 No. Q²¹ Q²² Q²³ Q²⁴ R²¹ R²² R²³ R²⁴ A² 181 Br Br Br Br SMe SMe SMe SMe Formula (A2-2) 182 Br Br Br Br SMe 2-SEt SMe 2-SEt Formula (A2-2) 183 Br Br Br Br SMe 3-S^(n)Pr SMe 3-S^(n)Pr Formula (A2-2) 184 Br Br Br Br SMe 4-S^(n)Bu SMe 4-S^(n)Bu Formula (A2-2) 185 Br Br Br Br 2-SEt 2-SEt 2-SEt 2-SEt Formula (A2-2) 186 Br Br Br Br 2-SEt 3-S^(n)Pr 2-SEt 3-S^(n)Pr Formula (A2-2) 187 Br Br Br Br 2-SEt 4-S^(n)Bu 2-SEt 4-S^(n)Bu Formula (A2-2) 188 Br Br Br Br 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-2) 189 Br Br Br Br 3-S^(n)Pr 4-S^(n)Bu 3-S^(n)Pr 4-S^(n)Bu Formula (A2-2) 190 Br Br Br Br 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu 4-S^(n)Bu Formula (A2-2) 191 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-1), n = 2, Z = NH 192 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-1), n = 2, Z = S 193 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-1), n = 3, Z = NH 194 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-1), n = 3, Z = S 195 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-3), Z = NH 196 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-3), Z = S 197 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-4), Z = NH 198 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-4), Z = S 199 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-5), Z = NH 200 F F Cl Cl 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr 3-S^(n)Pr Formula (A2-5), Z = S

Preferred compounds represented by the above formula (2) include, for example, one in which in the above formula (2-1), Q²¹ to Q²⁴ are chlorine atoms, x is 3, and A² is a 1,4-piperazinediyl group.

With regard to all components and items described above, combinations of those preferred are more preferred, and combinations of those more preferred are even more preferred. The same applies to combinations of those preferred and those more preferred and the like.

The compound represented by the above formula (2) can be manufactured as follows. It should be noted that Q²¹ to Q²⁴, R²¹ to R²⁴, and A² which may be used appropriately in the following formulae (20-1) to (24) each have the same meanings as defined in the above formula (2).

First, a compound represented by the following formula (20-1) obtained in accordance with the method described in Japanese Unexamined Patent Application Publication No. 2004-75719 by using 2-amino-4-halogenophenol as a raw material is converted into a methyl-ω-sulfonic acid derivative represented by the following formula (21) using sodium bisulfite and formalin. Then, the resulting methyl-ω-sulfonic acid derivative represented by the following formula (21) and a compound represented by the following formula (22) diazotized according to the conventional method are subjected to a coupling reaction at a reaction temperature of 0 to 15° C. and at pH 4 to 6. Subsequently, a hydrolysis reaction is performed at a reaction temperature of 80 to 95° C. and at pH 10.5 to 11.5 to obtain a compound represented by the following formula (23-1). Further, compounds represented by the following formulae (23-2) to (23-4) are obtained as described above except that compounds represented by the following formulae (20-2) to (20-4) are used instead of the compound represented by the following formula (20-1).

Subsequently, the compound (1 equivalent) represented by the above formula (23-1), the compound (1 equivalent) represented by the above formula (23-2), and a cyanuric halide (such as cyanuric chloride, 1 equivalent) are condensed at a reaction temperature of 15 to 45° C. and at pH 5 to 8 to obtain a compound represented by the following formula (24-1). It should be noted that one of the compounds (1 equivalent) represented by the above formula (23-1) and the compound (1 equivalent) represented by the above formula (23-2) may be reacted with a cyanuric halide (1 equivalent), and then the resulting reaction product may further be reacted with the other compound. Further, a compound represented by the following formula (24-2) is obtained as described above except that compounds represented by the above formulae (23-3) and (23-4) are used instead of the compounds represented by the above formulae (23-1) and (23-2).

Subsequently, the compound (1 equivalent) represented by the above formula (24-1), the compound (1 equivalent) represented by the above formula (24-2), and a compound represented by a formula H-A²-H may be reacted at a reaction temperature of 55 to 95° C. and at pH 6 to 9 to cause a de-HCl reaction. This can lead to production of the compound represented by the above formula (2). It should be noted that one of the compounds (1 equivalent) represented by the above formula (24-1) and the compound (1 equivalent) represented by the above formula (24-2) may be reacted with the compound represented by the formula H-A²-H, and then the resulting reaction product may further be reacted with the other compound.

[Salt and the Like of Compound Represented by Formula (1) or (2)]

Salts of the compound represented by the above formula (1) or (2) include salts with inorganic or organic cations. Specific examples of salts with inorganic cations include alkali metal salts such as lithium salts, sodium salts, and potassium salts; ammonium salts; and the like. Specific examples of organic cations include, but are not limited to, for example, quaternary ammonium represented by the following formula (3)

In the above formula (3), each Z¹ to Z⁴ independently represents a hydrogen atom, a C1-C4 alkyl group, a hydroxy C1-C4 alkyl group, or a hydroxy C1-C4 alkoxy C1-C4 alkyl group, and at least one of Z¹ to Z⁴ is a group other than a hydrogen atom.

Specific examples of the C1-C4 alkyl group in Z¹ to Z⁴ include a methyl group, an ethyl group and the like. Similarly, specific examples of the hydroxy C1-C4 alkyl group include a hydroxymethyl group, a hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 4-hydroxybutyl group, a 3-hydroxybutyl group, a 2-hydroxybutyl group and the like. Similarly, specific examples of the hydroxy C1-C4 alkoxy C1-C4 alkyl group include a hydroxyethoxymethyl group, a 2-hydroxyethoxyethyl group, a 3-(hydroxyethoxy)propyl group, a 3-(hydroxyethoxy)butyl group, a 2-(hydroxyethoxy)butyl group and the like.

Among the above salts, preferred are alkali metal salts such as sodium salts, potassium salts, lithium salts; organic quaternary ammonium salts such as monoethanolamine salts, diethanolamine salts, triethanolamine salts, monoisopropanolamine salts, diisopropanolamine salts, triisopropanolamine salts; ammonium salts; and the like. More preferred are lithium salts, sodium salts, and ammonium salts. It is generally known that a salt of a compound may be responsible for varied physical properties such as solubility and/or varied ink performances when used in an ink, depending on the type of the salt. Therefore, the type of a salt may also be preferably selected according to the target ink performance and the like. A salt of the compound represented by the above formula (1) or (2) may be any of a single salt; a mixture of a plurality of salts; a mixture of a free acid and a single or a plurality of salts; and the like.

The compound represented by the above formula (1) or (2) may be able to take various isomeric structures such as tautomers, geometrical isomers, optical isomers, and structural isomers. If that is the case, the compound represented by the above formula (1) or (2) can be used in any of these structures or under a condition where two or more of these structures are co-presented. The term “tautomer” refers to one of a set of two or more generally known isomers for one compound which can readily undergo interconversion from one to another. The term “geometrical isomer” refers to, for example, a type of generally known stereoisomers, and refers to cis-trans isomers in the case of an organic compound. The term “optical isomer” refers to, for example, a type of generally known stereoisomers, and refers to a substance having different orientations of a rotatory polarization, including a left-handed enantiomer, a right-handed enantiomer, and a racemic compound. The term “structural isomer” refers to, for example, a type of generally known isomers, and refers to a molecule having the same composition formula but a different inter-atomic bonding pattern.

[Ink]

The ink according to the present invention contains the compound represented by the above formula (1) or (2). The above ink can be prepared by dissolving the compound represented by the above formula (1) or (2) in an aqueous medium (water or a solution mixture of water and a water-soluble organic solvent), and adding an ink preparation agent, if desired.

The ink may further include a known yellow coloring matter other than the compound represented by the above formula (1) or (2) for a purpose of finely adjusting the hue thereof in a range where the effects of the present invention are not impaired. The compound represented by the above formula (1) or (2) may also be used, for example, in combination with known coloring matters of magenta, cyan and the like for a purpose of preparing various color inks such as black, red, and green.

When used as an ink-jet ink, the ink preferably has a smaller content of inorganic impurities. Inorganic impurities may be, for example, chlorides of metal cations (sodium chloride and the like), sulfates (sodium sulfate and the like) and the like. The total content of inorganic impurities may usually be 1% by mass or less relative to the total mass of the compound represented by the above formula (1) or (2), and the lower limit may be 0% by mass, i.e., less than or equal to the detection limit of a detector. Methods of reducing the content of inorganic impurities in a coloring matter include, for example, those involving purification of a coloring matter with reverse osmotic membrane, by crystallization, by suspension purification and the like.

A water-soluble organic solvent may have the following effects of: dissolving a coloring matter; preventing a composition from drying (maintaining a wet condition); adjusting the viscosity of a composition; promoting permeation of a coloring matter into a recording medium; adjusting the surface tension of a compound; defoaming a compound; and the like. Therefore, the above ink preferably contains a water-soluble organic solvent.

Examples of the above water-soluble organic solvent include, for example, C1-C4 alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, secondary butanol, tertiary butanol; amides such as N,N-dimethylformamide, N,N-dimethylacetamide; heterocyclic ketones such as 2-pyrrolidone, N-methyl-2-pyrrolidone, hydroxyethyl-2-pyrrolidone, 1,3-dimethylimidazolidin-2-one, 1,3-dimethylhexahydropyrimid-2-one; ketones or keto alcohols such as acetone, methyl ethyl ketone, 2-methyl-2-hydroxypentan-4-one; cyclic ethers such as tetrahydrofuran, dioxane; mono-, oligo- or polyalkylene glycol or thioglycol having a C2-C6 alkylene unit such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 1,2-butanediol, 1,4-butanediol, 1,2-pentanediol, 1,5-pentanediol, 1,2-hexandiol, 1,6-hexylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, thiodiglycol; polyols (preferably triols) such as trimethylolpropane, glycerin, hexane-1,2,6-triol; C1-C4 monoalkyl ethers of polyhydric alcohols such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether (butylcarbitol), triethylene glycol monomethyl ether, triethylene glycol monoethyl ether; γ-butyrolactone; dimethyl sulfoxide; and the like.

It should be noted that a substance, for example, trimethylolpropane and the like that is solid at ambient temperature is also contained in the above water-soluble organic solvent. That is, when an aqueous solution containing a substance that is solid at ambient temperature but is water soluble has similar characteristics to those of the water-soluble organic solvents, and therefore can be used with expectation of the same effects, that substance shall fall within the category of the water-soluble organic solvents.

Such substances include, for example, solid polyhydric alcohols, saccharides, amino acids and the like.

Ink preparation agents include, for example, known additives such as antiseptic and antifungal agents, pH adjusting agents, chelating reagents, rust-preventive agents, ultraviolet absorbing agents, viscosity adjusting agents, dye-dissolving agents, anti-fading agents, surface tension adjusting agents, defoaming agents and the like.

Examples of the aforementioned antiseptic and antifungal agents include, for example, organic sulfur-based, organic nitrogen sulfur-based, organic halogen-based, haloallylsulfone-based, iodopropargyl-based, N-haloalkylthio-based, benzothiazole-based, nitrile-based, pyridine-based, 8-oxyquinoline-based, isothiazoline-based, dithiol-based, pyridinoxide-based, nitropropane-based, organic tin-based, phenol-based, quaternary ammonium salt-based, triazine-based, thiadiazine-based, anilide-based, adamantane-based, dithiocarbamate-based, brominated indanon-based, benzyl bromoacetate-based, inorganic salt-based compounds and the like. Examples of the organic halogen-based compound include, for example, sodium pentachlorophenol. Examples of the pyridinoxide-based compound include, for example, sodium 2-pyridinethiol-1-oxide. Examples of the isothiazoline-based compound include, for example, 1,2-benzisothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one magnesium chloride, 5-chloro-2-methyl-4-isothiazolin-3-one calcium chloride, 2-methyl-4-isothiazolin-3-one calcium chloride and the like. Other antiseptic and antifungal agents include sodium acetate, sodium sorbate, sodium benzoate, and Proxel™ series (Proxel™ GXL (S), Proxel™ XL-2 (S) and the like), which are product names and available from Arch Chemicals, Inc.

Any substance can be used as a pH adjusting agent as long as it can control the pH of an ink within the range between 6.0 and 11.0 for the purpose of improving the storage stability of the ink. Examples include alkanolamines such as diethanolamine, triethanolamine; hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide, potassium hydroxide; ammonium hydroxide; carbonates of alkali metals such as lithium carbonate, sodium carbonate, potassium carbonate; aminosulfonic acid such as taurine; and the like.

Examples of the chelating reagent include, for example, disodium ethylenediaminetetraacetate, sodium nitrilotriacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, sodium uracildiacetate and the like.

Examples of the rust preventive agent include, for example, hydrogen sulfite salt, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, dicyclohexylammonium nitrite and the like.

Examples of the ultraviolet absorbing agent include, for example, benzophenone-based compounds, benzotriazole-based compounds, cinnamic acid-based compounds, triazine-based compounds, stilbene-based compounds and the like. In addition, a compound which absorbs ultraviolet light and emits fluorescence, so-called fluorescent whitening agents, represented by benzoxazole-based compounds, can also be used.

Examples of the viscosity adjusting agent include, in addition to water-soluble organic solvents, water-soluble polymer compounds such as, polyvinyl alcohol, cellulose derivatives, polyamine, polyimine and the like.

Examples of the dye-dissolving agents include, for example, urea, s-caprolactam, ethylene carbonate and the like.

An anti-fading agent is used for the purpose of improving the preserving property of images. As the anti-fading agent, various organic and metal complex-based anti-fading agents can be used. Examples of the organic anti-fading agent include, for example, hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indans, chromans, alkoxyanilines, heterocycles and the like. Examples of the metal complex-based anti-fading agent include, for example, nickel complexes, zinc complexes and the like.

Examples of the surface tension adjusting agent include surfactants. Surfactants include, for example, anionic surfactants, amphoteric surfactants, cationic surfactants, nonionic surfactants and the like.

Examples of the anionic surfactant include, for example, alkylsulfocarboxylate, α-olefin sulfonate, polyoxyethylene alkyl ether acetate, N-acylamino acid and a salt thereof, N-acylmethyltaurine salt, alkylsulfate polyoxyalkyl ether sulfate, alkylsulfate polyoxyethylene alkyl ether phosphate, rosin acid soap, castor oil sulfate ester salt, lauryl alcohol sulfate ester salt, alkylphenol-type phosphate ester, alkyl-type phosphate ester, alkylallylsulfonate, diethyl sulfosuccinate, diethylhexyl sulfosuccinate, dioctyl sulfosuccinate and the like.

Examples of the cationic surfactant include, for example, 2-vinylpyridine derivatives, poly 4-vinylpyridine derivatives and the like.

Examples of the amphoteric surfactant include, for example, lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine, coconut oil fatty acid amide propyldimethylaminoacetic acid betaine, polyoctylpolyaminoethylglycine, and in addition, imidazoline derivatives and the like.

Examples of the nonionic surfactant include, for example, those based on ether such as polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene dodecylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene alkyl ether; those based on ester such as polyoxyethylene oleate ester, polyoxyethylene distearate ester, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, polyoxyethylene stearate; those based on acetylene glycols (alcohols) such as 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3,6-diol, 3,5-dimethyl-1-hexyn-3-ol; Surfynol® 104, 82, 465, Olfine® STG, which are product names and available from Nissin Chemical Industry Co., Ltd.; Tergitol® 15-S-7, which is a product name and available from SIGMA-ALDRICH; and the like.

Examples of the defoaming agent include, for example, highly oxidized oil-based compounds, glycerine fatty acid ester-based compounds, fluorine-based compounds, silicone-based compounds and the like.

The total content of the compound represented by the above formula (1) or (2) in an ink is usually 0.1 to 20% by mass relative to the total mass of the ink, preferably 1 to 10% by mass, and more preferably 2 to 8% by mass. Similarly, the content of a water-soluble organic solvent is usually 0 to 60% by mass, preferably 10 to 50% by mass. Similarly, the content of an ink preparation agent is usually 0 to 20% by mass, preferably 0 to 15% by mass. The present ink contains the compound represented by the above formula (1) or (2), and, if desired, a water-soluble organic solvent and an ink preparation agent, the remainder other than these being water.

The surface tension of the present ink is usually 25 to 70 mN/m, preferably 25 to 60 mN/m. The viscosity of the present ink is preferably 30 mPa·s or less, more preferably 20 mPa·s or less.

The present ink can be prepared by mixing each of the above components as required. There is no particular limitation for the order of adding each component. Water with little impurities such as ion exchange water, distilled water is preferably used for preparing the present ink. Further, the present ink after preparation may be subjected to precision filtration through a membrane filter and the like. When the present ink is used as an ink-jet ink, precision filtration is preferably performed for a purpose of preventing clogging of a nozzle and the like. The pore diameter of a filter used for precision filtration is usually 1 to 0.1 μm, preferably 0.8 to 0.1 μm.

The present ink may be used for various applications such as textile printing, copying, marking, writing, drawing, stamping, and recording. Among these applications, it is suitably used for ink-jet recording.

[Ink-Jet Recording Method, Ink-Jet Printer, and Recording Medium]

The ink-jet recording method according to the present invention includes discharging a droplet of the ink according to the present invention in response to a recording signal to allow for attachment to a recording medium. Ink-jet systems include, for example, piezo systems, thermal ink-jet systems and the like. The ink according to the present invention can be used as an ink-jet ink for any system.

In the ink-jet recording method according to the present invention, the ink according to the present invention may be used alone or in combination with another ink. For example, one or two or more of inks selected from magenta, cyan, green, blue (or violet), red, black and the like can also be used along with the ink according to the present invention in order to obtain full-color recorded images.

Recording media may be classified broadly into those having ink receiving layers and those having no ink receiving layers. Either of them may be preferred as recording media for use in the ink-jet recording method. Specific examples of the recording medium include, for example, paper, film, fiber or cloth (cellulose, nylon, wool and the like), leather, a substrate for a color filter and the like.

An ink receiving layer may be provided on a recording medium in order to achieve an effect of absorbing an ink for accelerated drying of the ink. An ink receiving layer may be provided, for example, by a method in which a cation-based polymer is impregnated or applied on the above recording medium; a method in which inorganic particles capable of absorbing a coloring matter in an ink is applied on a surface of a recording medium along with a hydrophilic polymer such as polyvinyl alcohol and polyvinylpyrrolidone; and the like. Inorganic particles capable of absorbing a coloring matter in an ink include porous silica, alumina sol, special ceramics and the like. A recording medium having such an ink receiving layer is commonly called an ink-jet paper, an ink-jet film, a glossy paper, a glossy film and the like. Examples of typical commercial products of recording media having ink receiving layers include: Professional photograph paper, Canon photograph paper Glossy Pro [platinum grade], and Glossy Gold, which are product names and available from Canon, Inc.; Photograph paper Crispia (high-glossy), Photograph paper (glossy), which are product names and available from Seiko Epson Corporation; Advanced photograph paper (glossy), which is a product name and available from Hewlett Packard Japan Inc.; Gasai Photo-finishing Pro, which is a product name and available from FUJIFILM Corporation; Photograph glossy Paper BP71G from Brother Industries, Ltd.; and the like.

Examples of paper having no ink receiving layer include plain paper and the like. Among the commercially available plain paper, those for ink-jet recording include Double-sided high quality plain paper (Seiko Epson Corporation); PB PAPER GF-500 (Canon, Inc.); Multipurpose Paper, All-in-one Printing Paper (Hewlett Packard); and the like. Plain paper copier (PPC) paper and the like also fall within the category of the plain paper.

Among these, a recording medium to which either

(a) the compound represented by the above formula (1) or (2) and

(b) an ink containing the compound represented by the above formula (1) or (2) is attached falls within the scope of the present invention. Further, an ink-jet printer loaded with a container containing an ink including the compound represented by the above formula (1) or (2) falls within the scope of the present invention.

With regard to all components and items described above, combinations of those preferred are more preferred, and combinations of those more preferred are even more preferred. The same applies to combinations of those preferred and those more preferred and the like.

The compound represented by the above formula (1) or (2) according to the present invention has excellent solubility in water and a solution mixture of water and a water-soluble organic solvent. Further, the ink according to the present invention is characterized by, for example, good filterability through a membrane filter. The ink according to the present invention can create extremely vivid recorded images having high color saturation and printing density with the ideal hue of yellow color when recorded on various recording media. Therefore, full-color images with photographic quality can be faithfully reproduced on a recording medium. The ink according to the present invention does not show solid precipitation, changes in physical properties, changes in a hue and the like after prolonged storage, demonstrating very good storage stability. The ink according to the present invention rarely shows solid precipitation upon drying. Therefore, the ink according to the present invention less likely causes clogging of a jetting unit (recording head) of an ink-jet printer. The ink according to the present invention does not change its physical properties even when used in a continuous ink-jet printer that uses a recirculated ink for relatively prolonged time intervals or even when used intermittently with an on-demand ink-jet printer. An image recorded on a recording medium having an ink receiving layer using the ink according to the present invention shows various aspects of roughness such as water resistance, moisture resistance, ozone gas resistance, abrasion resistance, and light resistance. In particular, it has good light resistance. This can also lead to an image recorded with photographic quality having excellent long-term storage stability. An image recorded on a recording medium having no ink receiving layer using the ink according to the present invention also shows excellent color saturation, brightness, and color-developing properties such as printing density.

EXAMPLES

Below, the present invention will be described more specifically with reference to Examples, but the present invention shall not be limited to these Examples. In Examples, the term “reaction temperature” refers to a temperature inside a reaction system. Unless otherwise specifically stated, various operations such as a reaction were all performed with stirring. Further, the term “Amax (maximal absorption wavelength)” refers to a value measured in an aqueous solution at pH 7 to 8, and was reported after being rounded off to one decimal place. It should be noted that the solubilities of the compounds according to the present invention obtained from Examples were 100 g/L or more in water at room temperature.

Example 1

(Step 1)

First, 20.8 parts of 5-amino-2-chlorobenzenesulfonic acid was dissolved in 200 parts of water while adjusting pH to 6 with sodium hydroxide, and 7.2 parts of sodium nitrite was then added. The solution was added dropwise to 200 parts of 5% hydrochloric acid over 30 minutes at 0 to 10° C., a diazotization reaction was performed with stirring at 10° C. or below for 1 hour to prepare a diazo reaction liquid.

Meanwhile, 26.6 parts of 2-(sulfopropoxy)-5-chloroaniline was dissolved in 130 parts of water while adjusting pH to 7 with sodium hydroxide, and a methyl-ω-sulfonic acid derivative was obtained by the conventional method using 10.4 parts of sodium bisulfite and 8.6 parts of 35% formalin. The resulting methyl-ω-sulfonic acid derivative was added to the diazo reaction liquid prepared above, and stirred for 24 hours under the conditions of 0 to 15° C. and pH 2 to 4. After adjusting pH to 11 with sodium hydroxide, the reaction liquid was stirred for 5 hours at 80 to 95° C. while maintaining that pH, and 100 parts of sodium chloride was added to perform salt precipitation. The resulting precipitated solid was then filtered and separated to obtain 100 parts of a compound represented by the following formula (100) as a wet cake.

(Step 2)

To 250 parts of ice water, 0.10 parts of Leocol® TD90 (surfactant), which is a product name and available from Lion Corporation, was added and vigorously stirred. 3.6 parts of cyanuric chloride was added thereto and stirred for 30 minutes at 0 to 5° C. to obtain a suspension liquid. Subsequently, 100 parts of the wet cake of the compound represented by the above formula (100) was dissolved in 200 parts of water to obtain a solution, to which the above suspension liquid was added dropwise over 30 minutes. After the completion of the dropwise addition, it was stirred for 6 hours under the conditions of pH 6 to 8 and 25 to 45° C. To the resulting liquid, 6.2 parts of 4-amino-2-methyl-1-butanol was added, and stirred for 4 hours under the conditions of pH 7 to 9 and 75 to 90° C. After cooling the resulting reaction liquid to 20 to 25° C., 2000 parts of 2-propanol was added to this reaction liquid, and stirred for 2 hours at 20 to 25° C. The resulting precipitated solid was filtered and separated to obtain 50.0 parts of a wet cake. By drying this wet cake with an 80° C. hot-air dryer, 11.5 parts of a sodium salt of a compound according to the present invention represented by the following formula (101) (λmax: 416.6 nm) was obtained.

Example 2

A sodium salt of a compound according to the present invention represented by the following formula (103) (λmax: 418.4 nm) in an amount of 11.3 parts was obtained as in Example 1 except that 5.3 parts of DL-2-amino-1-butanol was used instead of 6.2 parts of 4-amino-2-methyl-1-butanol in Example 1 (Step 2).

[Preparation of Ink]

Components shown in Table 47 below were mixed to obtain solutions, which were then subjected to precision filtration through 0.45 μm membrane filters to prepare inks of Examples 1, 2 and Comparative Examples 1, 2. The numerical values in the table are in terms of “parts,” and the symbol “-” means that that component is not included. In Table 47 below, the component “aq. NaOH” is indicated as “remainder”. This means that 25% aqueous sodium hydroxide and water were added to a liquid mixture of each component so that the resulting liquid had a total amount of 100 parts and a pH of 8.0 to 9.5.

Abbreviations in Tables 47 have the following meanings.

Formula (101): a compound represented by the above formula (101)

Formula (102): a compound represented by the above formula (102)

Formula (300): a compound represented by the following formula (300)

DY132: C.I. Direct Yellow 132

EDTA2Na: disodium ethylenediaminetetraacetate

104PG50: Surfynol 104PG50 (Air Products and Chemicals, Japan, Inc.)

TABLE 47 Example Comparative Example Component 1 2 1 2 Formula (101) 3 — — — Formula (102) — 3 — — Formula (300) — — 3 — DY132 — — — 3 Glycerin 5 5 5 5 Urea 5 5 5 5 N-methyl-2-pyrrolidone 4 4 4 4 Isopropyl alcohol 3 3 3 3 Butylcarbitol 2 2 2 2 Taurine 0.3 0.3 0.3 0.3 EDTA2Na 0.1 0.1 0.1 0.1 104PG50 0.1 0.1 0.1 0.1 aq. NAOH Remainder Remainder Remainder Remainder Total 100 100 100 100 [Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Examples 1, 2 and Comparative Examples 1, 2 to be attached on the following glossy papers 1 to 4. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, platinum grade (PT-201)

Glossy paper 2: Seiko Epson Corporation, Product name: Photograph paper Crispia

Glossy paper 3: Brother Industries, Ltd., Product name: BP71G

Glossy paper 4: FUJIFILM Corporation, Product name: Gasai Photo-finishing Pro

[Color Measurements of Recorded Image]

When required, color measurements were performed for a recorded image using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of ANSI A, a wide viewing angle of 2 degrees, a light source of D50.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 55% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 3-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 48 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 85% or more: A A coloring matter persistence rate of 81% or more and less than 85%: B

A coloring matter persistence rate of less than 81%: C

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 48 Results from light Glossy paper resistance tests 1 2 3 4 Example 1 A B A A 2 B A A B Comparative 1 B B B C Example 2 B C B B

As clearly seen in Table 48, Examples 1, 2 showed better results than Comparative Examples 1, 2 for each glossy paper in the light resistance tests.

Example 3

A sodium salt of a compound according to the present invention represented by the following formula (103) (λmax: 418.5 nm) was obtained in an amount of 11.2 parts as in Example 1 except that 4.5 parts of 2-(methylamino)ethanol was used instead of 6.2 parts of 4-amino-2-methyl-1-butanol in Example 1 (Step 2).

[Preparation of Ink]

An ink of Example 3 was prepared as in Example 1 except that the compound represented by the above formula (103) was used instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Example 3 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1 to 4. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, platinum grade (PT-201)

Glossy paper 2: Seiko Epson Corporation, Product name: Photograph paper Crispia

Glossy paper 3: Brother Industries, Ltd., Product name: BP71G

Glossy paper 4: FUJIFILM Corporation, Product name: Gasai Photo-finishing Pro

[Color Measurements of Recorded Image]

When required, color measurements were performed for a recorded image using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of DIN NB, a wide viewing angle of 2 degrees, a light source of D65.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 70% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 4-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 49 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 90% or more: A

A coloring matter persistence rate of 85% or more and less than 90%: B

A coloring matter persistence rate of 81% or more and less than 85%: C

A coloring matter persistence rate of less than 81%: D

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 49 Results from light Glossy paper resistance tests 1 2 3 4 Example 3 A A A A Comparative 1 C B D B Example 2 C D D D

As clearly seen in Table 49, Examples 3 showed better results than Comparative Examples 1, 2 for each glossy paper in the light resistance tests.

Example 4

(Step 1)

While adjusting pH to 7 with sodium hydroxide, 17.3 parts of 5-amino-2-chlorobenzenesulfonic acid was dissolved in 200 parts of water, and 7.2 parts of sodium nitrite was then added. This solution was added dropwise to 200 parts of 5% hydrochloric acid over 30 minutes at 0 to 10° C., a diazotization reaction was performed with stirring for 1 hour at 10° C. or below to prepare a diazo reaction liquid.

Meanwhile, 26.6 parts of 2-(sulfopropoxy)-5-chloroaniline was dissolved in 130 parts of water while adjusting pH to 7 with sodium hydroxide, and a methyl-ω-sulfonic acid derivative was obtained by the conventional method using 10.4 parts of sodium bisulfite and 8.6 parts of 35% formalin. The resulting methyl-ω-sulfonic acid derivative was added to the diazo reaction liquid prepared above, and stirred for 24 hours under the conditions of 0 to 15° C. and pH 4 to 6. After adjusting pH to 11 with sodium hydroxide, the reaction liquid was stirred for 5 hours at 80 to 95° C. while maintaining that pH, and 100 parts of sodium chloride was added to perform salt precipitation. The resulting precipitated solid was then filtered and separated to obtain 100 parts of the compound represented by the above formula (100) as a wet cake.

(Step 2)

To 250 parts of ice water, 0.10 parts of Leocol® TD90 (surfactant), which is a product name and available from Lion Corporation, was added and vigorously stirred. 3.6 parts of cyanuric chloride was added thereto and stirred for 30 minutes at 0 to 5° C. to obtain a suspension liquid. Subsequently, 100 parts of the wet cake of the compound represented by the above formula (100) was dissolved in 200 parts of water to obtain a solution, to which the above suspension liquid was added dropwise over 30 minutes. After the completion of the dropwise addition, it was stirred for 6 hours under the conditions of pH 6 to 8 and 25 to 45° C. To the resulting liquid, 3.4 parts of 3-methoxypropylamine was added, and stirred for 2 hours under the conditions of pH 7 to 9 and 75 to 90° C. After cooling the resulting reaction liquid to 20 to 25° C., 2000 parts of 2-propanol was added to this reaction liquid, and stirred for 2 hours at 20 to 25° C. The resulting precipitated solid was filtered and separated to obtain 103.3 parts of a wet cake. By drying this wet cake with an 80° C. hot-air dryer, 13.3 parts of a sodium salt of a compound according to the present invention represented by the following formula (104) (λmax: 408.0 nm) was obtained.

[Preparation of Ink]

An ink of Example 4 was prepared as in Example 1 except that the compound represented by the above formula (104) was used instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Examples 4 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1 to 4. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, platinum grade (PT-201)

Glossy paper 2: Seiko Epson Corporation, Product name: Photograph paper Crispia

Glossy paper 3: Brother Industries, Ltd., Product name: BP71G

Glossy paper 4: FUJIFILM Corporation, Product name: Gasai Photo-finishing Pro

[Color Measurements of Recorded Image]

When required, color measurements of a recorded image were performed using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of DIN NB, a wide viewing angle of 2 degrees, a light source of D65.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 55% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 3-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 50 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 85% or more: A

A coloring matter persistence rate of 81% or more and less than 85%: B

A coloring matter persistence rate of less than 81%: C

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 50 Results from light Glossy paper resistance tests 1 2 3 4 Example 4 A A A A Comparative 1 B B B C Example 2 B C C C

As clearly seen in Table 50, Examples 4 showed better results than Comparative Examples 1, 2 for each glossy paper in the light resistance tests.

Example 5

A sodium salt of a compound according to the present invention represented by the following formula (105) (λmax: 419.0 nm) was obtained in an amount of 10.5 parts as in Example 1 except that 6.0 parts of 1-amino-2-propanol was used instead of 6.2 parts of 4-amino-2-methyl-1-butanol in Example 1 (Step 2).

Example 6

A sodium salt of a compound according to the present invention represented by the following formula (106) (λmax: 418.0 nm) was obtained in an amount of 10.2 parts as in Example 1 except that 6.0 parts of 2-amino-1-propanol was used instead of 6.2 parts of 4-amino-2-methyl-1-butanol in Example 1 (Step 2).

Example 7

A sodium salt of a compound according to the present invention represented by the following formula (107) (λmax: 418.5 nm) was obtained in an amount of 5.6 parts as in Example 1 except that 6.2 parts of 2-amino-2-methyl-1-propanol was used instead of 6.2 parts of 4-amino-2-methyl-1-butanol in Example 1 (Step 2).

Example 8

A sodium salt of a compound according to the present invention represented by the following formula (108) (λmax: 418.5 nm) was obtained in an amount of 11.2 parts as in Example 1 except that 6.2 parts of ethoxypropylamine was used instead of 6.2 parts of 4-amino-2-methyl-1-butanol in Example 1 (Step 2).

[Preparation of Ink]

Inks of Examples 5 to 8 were prepared as in Example 1 except that the compounds represented by the above formulae (105) to (108) were used, respectively, instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Examples 5 to 8 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1 to 6. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, platinum grade (PT-201)

Glossy paper 2: Canon, Inc., Product name: Canon Photograph paper, gold grade (GL-101)

Glossy paper 3: Seiko Epson Corporation, Product name: Photograph paper Crispia

Glossy paper 4: Seiko Epson Corporation, Product name: Photograph paper <glossy>

Glossy paper 5: Brother Industries, Ltd., Product name: BP71G

Glossy paper 6: FUJIFILM Corporation, Product name: Gasai Photo-finishing Pro

[Color Measurements of Recorded Image]

When required, color measurements of a recorded image were performed using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of ANSI A, a wide viewing angle of 2 degrees, a light source of D50.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 70% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 4-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 51 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 90% or more: A

A coloring matter persistence rate of 85% or more and less than 90%: B

A coloring matter persistence rate of 81% or more and less than 85%: C

A coloring matter persistence rate of less than 81%: D

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 51 Results from light Glossy paper resistance tests 1 2 3 4 5 6 Example 5 C B C B B B 6 B A B A A B 7 C B B B C B 8 A A A A B B Comparative 1 C B C B C B Example 2 C D C C C C

As clearly seen in Table 51, Examples 5 to 8 showed better results than Comparative Examples 1, 2 for each glossy paper in the light resistance tests.

Example 9

To 250 parts of ice water, 0.10 parts of Leocol® TD90 (surfactant), which is a product name and available from Lion Corporation, was added and vigorously stirred. 3.6 parts of cyanuric chloride was added thereto and stirred for 30 minutes at 0 to 5° C. to obtain a suspension liquid. Subsequently, 100 parts of the wet cake of the compound represented by the above formula (100) was dissolved in 200 parts of water to obtain a solution, to which the above suspension liquid was added dropwise over 30 minutes. After the completion of the dropwise addition, it was stirred for 6 hours under the conditions of pH 6 to 8 and 25 to 45° C. To the resulting liquid, 5.0 parts of methylamine hydrochloride was added, and stirred for 2 hours under the conditions of pH 7 to 9 and 75 to 90° C. After cooling the resulting reaction liquid to 20 to 25° C., 2000 parts of 2-propanol was added to this reaction liquid, and stirred for 2 hours at 20 to 25° C. The resulting precipitated solid was filtered and separated to obtain 48.6 parts of a wet cake. By drying this wet cake with an 80° C. hot-air dryer, 10.9 parts of a sodium salt of a compound according to the present invention represented by the following formula (109) (λmax: 418.0 nm) was obtained.

[Preparation of Ink]

An ink of Example 9 was prepared as in Example 1 except that the compound represented by the above formula (109) was used instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Example 9 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1 to 4. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, platinum grade (PT-201)

Glossy paper 2: Seiko Epson Corporation, Product name: Photograph paper Crispia

Glossy paper 3: Brother Industries, Ltd., Product name: BP71G

Glossy paper 4: FUJIFILM Corporation, Product name: Gasai

Photo-Finishing Pro

[Color Measurements of Recorded Image]

When required, color measurements of a recorded image were performed using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of ANSI A, a wide viewing angle of 2 degrees, a light source of D50.

[Printing Density Tests]

Yellow printing density (Dy value) was measured using the above colorimetric system for each test piece at a gradation portion where the reflection density was highest. A larger numerical value indicates superior color-developing properties. Evaluation results are shown in Table 52 below.

TABLE 52 Results from printing Glossy paper density tests 1 2 3 4 Example 9 2.19 2.21 2.10 2.16 Comparative 1 2.14 2.19 2.07 2.15 Example 2 2.12 2.14 2.03 2.05

As clearly seen in Table 52, Example 9 showed better results than Comparative Examples 1, 2 in the yellow printing density tests (Dy value) for each glossy paper.

Example 10

To 250 parts of ice water, 0.10 parts of Leocol® TD90 (surfactant) which is a product name and available from Lion Corporation, was added and vigorously stirred. 3.6 parts of cyanuric chloride was added thereto and stirred for 30 minutes at 0 to 5° C. to obtain a suspension liquid. Subsequently, 100 parts of the wet cake of the compound represented by the above formula (100) was dissolved in 200 parts of water to obtain a solution, to which the above suspension liquid was added dropwise over 30 minutes. After the completion of the dropwise addition, it was stirred for 6 hours under the conditions of pH 6 to 8 and 25 to 45° C. To the resulting liquid, 6.0 parts of ethylamine hydrochloride was added, and stirred for 2 hours under the conditions of pH 7 to 9 and 75 to 90° C. After cooling the resulting reaction liquid to 20 to 25° C., 2000 parts of 2-propanol was added to this reaction liquid, and stirred for 2 hours at 20 to 25° C. The resulting precipitated solid was filtered and separated to obtain 49.3 parts of a wet cake. By drying this wet cake with an 80° C. hot-air dryer, 11.0 parts of a sodium salt of a compound according to the present invention represented by the following formula (110) (λmax: 416.5 nm) was obtained.

Example 11

A sodium salt of a compound according to the present invention represented by the following formula (111) (λmax: 416.5 nm) was obtained in an amount of 11.2 parts as in Example 10 except that 4.4 parts of propylamine was used instead of 6.0 parts of ethylamine hydrochloride.

Example 12

A sodium salt of a compound according to the present invention represented by the following formula (112) (λmax: 418.0 nm) was obtained in an amount of 11.3 parts as in Example 10 except that 5.4 parts of butylamine was used instead of 6.0 parts of ethylamine hydrochloride.

[Preparation of Ink]

Inks of Examples 10 to 12 were prepared as in Example 1 except that the compounds represented by the above formulae (110) to (112) were used, respectively, instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Examples 10 to 12 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1 to 3. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, gold grade (GL-101)

Glossy paper 2: Seiko Epson Corporation, Product name: Photograph paper Crispia

Glossy paper 3: Brother Industries, Ltd., Product name: BP71G

[Color Measurements of Recorded Image]

When required, color measurements of a recorded image were performed using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of ANSI A, a wide viewing angle of 2 degrees, a light source of D50.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 70% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 3-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 53 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 85% or more: A

A coloring matter persistence rate of 81% or more and less than 85%: B

A coloring matter persistence rate of less than 81%: C

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 53 Results from light Glossy paper resistance tests 1 2 3 Example 10 A A A 11 A A B 12 A A B Comparative  1 A B B Example  2 C B B

As clearly seen in Table 53, Example 10 showed similar results for Glossy paper 1 and better results for Glossy papers 2, 3 as compared with Comparative Example 1. Further, Example 10 showed better results for each glossy paper as compared with Comparative Example 2. Examples 11, 12 showed similar results for Glossy papers 1, 3 and better results for Glossy paper 2 as compared with Comparative Example 1. Examples 11, 12 showed similar results for Glossy paper 3 and better results for Glossy papers 1, 2 as compared with Comparative Example 2. These results demonstrate that Examples 10 to 12 have similar or better light resistance as compared with Comparative Examples 1, 2.

Example 13

A sodium salt of a compound according to the present invention represented by the following formula (113) (λmax: 416.5 nm) was obtained in an amount of 11.0 parts as in Example 10 except that 15.0 parts of 2-amino-1,3-propanediol was used instead of 6.0 parts of ethylamine hydrochloride.

[Preparation of Ink]

An ink of Example 13 was prepared as in Example 1 except that the compound represented by the above formula (113) was used instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Example 13 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1 to 3. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, gold grade (GL-101)

Glossy paper 2: Seiko Epson Corporation, Product name: Photograph paper <glossy>

Glossy paper 3: FUJIFILM Corporation, Product name: Gasai Photo-finishing Pro

[Color Measurements of Recorded Image]

When required, color measurements of a recorded image were performed using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of ANSI A, a wide viewing angle of 2 degrees, a light source of D50.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 70% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 3-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 54 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 85% or more: A

A coloring matter persistence rate of 81% or more and less than 85%: B

A coloring matter persistence rate of less than 81%: C

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 54 Results from light Glossy paper resistance tests 1 2 3 Example 13 A A A Comparative  1 A B A Example  2 C B B

As clearly seen in Table 54, Example 13 showed similar results for Glossy papers 1, 3 and better results for Glossy paper 2 as compared with Comparative Example 1. Further, Example 13 showed better results for each glossy paper as compared with Comparative Example 2. These results demonstrate that Example 13 has similar or better light resistance as compared with Comparative Examples 1, 2.

Example 14

A sodium salt of a compound according to the present invention represented by the following formula (114) (λmax: 422.0 nm) was obtained in an amount of 11.3 parts as in Example 1 except that 5.3 parts of 2-(ethylamino)ethanol was used instead of 6.2 parts of 4-amino-2-methyl-1-butanol in Example 1 (Step 2).

Example 15

A sodium salt of a compound according to the present invention represented by the following formula (115) (λmax: 420.5 nm) was obtained in an amount of 11.6 parts as in Example 1 except that 7.0 parts of 2-(butylamino)ethanol was used instead of 6.2 parts of 4-amino-2-methyl-1-butanol in Example 1 (Step 2).

[Preparation of Ink]

Inks of Examples 14, 15 were prepared as in Example 1 except that the compounds represented by the above formulae (114), (115) were used, respectively, instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Examples 14, 15 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1 to 4. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, gold grade (GL-101)

Glossy paper 2: Seiko Epson Corporation, Product name: Photograph paper <glossy>

Glossy paper 3: Brother Industries, Ltd., Product name: BP71G

Glossy paper 4: FUJIFILM Corporation, Product name: Gasai Photo-finishing Pro

[Color Measurements of Recorded Image]

When required, color measurements of a recorded image were performed using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of ANSI A, a wide viewing angle of 2 degrees, a light source of D50.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 70% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 4-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 55 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 90% or more: A

A coloring matter persistence rate of 85% or more and less than 90%: B

A coloring matter persistence rate of 81% or more and less than 85%: C

A coloring matter persistence rate of less than 81%: D

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 55 Results from light Glossy paper resistance tests 1 2 3 4 Example 14 B A A A 15 B C B B Comparative  1 B C C C Example  2 D C C C

As clearly seen in Table 55, Example 14 showed similar results for Glossy paper 1 and better results for Glossy papers 2 to 4 as compared with Comparative Example 1. Further, Example 14 showed good results for each glossy paper as compared with Comparative Example 2. Example 15 showed similar results for Glossy papers 1, 2 and good results for Glossy papers 3, 4 as compared with Comparative Example 1. Further, Example 15 showed similar results for Glossy paper 2 and good results for the other glossy papers as compared with Comparative Example 2. These results demonstrate that Examples 14, 15 have similar or better light resistance as compared with Comparative Examples 1, 2.

Example 16

To 250 parts of ice water, 0.10 parts of Leocol® TD90 (surfactant), which is a product name and available from Lion Corporation, was added and vigorously stirred. 3.6 parts of cyanuric chloride was added thereto and stirred for 30 minutes at 0 to 5° C. to obtain a suspension liquid. Subsequently, 100 parts of the wet cake of the compound represented by the above formula (100) was dissolved in 200 parts of water to obtain a solution, to which the above suspension liquid was added dropwise over 30 minutes. After the completion of the dropwise addition, it was stirred for 6 hours under the conditions of pH 6 to 8 and 25 to 45° C. To the resulting liquid, 6.1 parts of tetrahydrofurfurylamine was added, and stirred for 2 hours under the conditions of pH 7 to 9 and 75 to 90° C. After cooling the resulting reaction liquid to 20 to 25° C., 2000 parts of 2-propanol was added to this reaction liquid, and stirred for 2 hours at 20 to 25° C. The resulting precipitated solid was filtered and separated to obtain 103.3 parts of a wet cake. By drying this wet cake with an 80° C. hot-air dryer, 11.4 parts of a sodium salt of a compound according to the present invention represented by the following formula (116) (λmax: 417.5 nm) was obtained.

[Preparation of Ink]

An ink of Example 16 was prepared as in Example 1 except that the compound represented by the above formula (116) was used instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Example 16 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1 to 4. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, platinum grade (PT-201)

Glossy paper 2: Canon, Inc., Product name: Canon Photograph paper, gold grade (GL-101)

Glossy paper 3: Seiko Epson Corporation, Product name: Photograph paper Crispia

Glossy paper 4: Brother Industries, Ltd., Product name: BP71G

[Color Measurements of Recorded Image]

When required, color measurements of a recorded image were performed using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of ANSI A, a wide viewing angle of 2 degrees, a light source of D50.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 55% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 4-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 56 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 90% or more: A

A coloring matter persistence rate of 85% or more and less than 90%: B

A coloring matter persistence rate of 81% or more and less than 85%: C

A coloring matter persistence rate of less than 81%: D

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 56 Results from light Glossy paper resistance tests 1 2 3 4 Example 16 B A B B Comparative  1 C B C C Example  2 C D C C

As clearly seen in Table 56, Example 16 showed good results for each glossy paper as compared with Comparative Examples 1, 2. These results demonstrate that Example 16 has superior light resistance as compared with Comparative Examples 1, 2.

Example 17

A sodium salt of a compound according to the present invention represented by the following formula (117) (λmax: 416.5 nm) was obtained in an amount of 10.5 parts as in Example 16 except that 4.0 parts of pyrrolidine was used instead of 6.1 parts of tetrahydrofurfurylamine.

[Preparation of Ink]

An ink of Example 17 was prepared as in Example 1 except that the compound represented by the above formula (117) was used instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Example 17 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1, 2. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, platinum grade (PT-201)

Glossy paper 2: FUJIFILM Corporation, Product name: Gasai Photo-finishing Pro

[Color Measurements of Recorded Image]

When required, color measurements of a recorded image were performed using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of ANSI A, a wide viewing angle of 2 degrees, a light source of D50.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 55% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 2-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 57 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 85% or more: A

A coloring matter persistence rate of less than 85%: B

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 57 Results from light Glossy paper resistance tests 1 2 Example 17 A A Comparative  1 B B Example  2 B B

As clearly seen in Table 57, Example 17 showed good results for each glossy paper as compared with Comparative Examples 1, 2. These results demonstrate that Example 17 has superior light resistance as compared with Comparative Examples 1, 2.

Example 18

(Step 1)

While adjusting pH to 7 with sodium hydroxide, 20.8 parts of 5-amino-2-chlorobenzenesulfonic acid was dissolved in 200 parts of water, and 7.2 parts of sodium nitrite was then added. This solution was added dropwise to 200 parts of 5% hydrochloric acid over 30 minutes at 0 to 10° C., a diazotization reaction was performed with stirring for 1 hour at 10° C. or below to prepare a diazo reaction liquid.

Meanwhile, 26.6 parts of 2-(sulfopropoxy)-5-chloroaniline was dissolved in 130 parts of water while adjusting pH to 7 with sodium hydroxide, and a methyl-ω-sulfonic acid derivative was obtained by the conventional method using 10.4 parts of sodium bisulfite and 8.6 parts of 35% formalin. The resulting methyl-ω-sulfonic acid derivative was added to the diazo reaction liquid prepared above, and stirred for 24 hours under the conditions of 0 to 15° C. and pH 4 to 6. After adjusting pH to 11 with sodium hydroxide, the reaction liquid was stirred for 5 hours at 80 to 95° C. while maintaining that pH, and 100 parts of sodium chloride was added to perform salt precipitation. The resulting precipitated solid was then filtered and separated to obtain 100 parts of the compound represented by the above formula (100) as a wet cake.

(Step 2)

To 250 parts of ice water, 0.10 parts of Leocol® TD90 (surfactant), which is a product name and available from Lion Corporation, was added and vigorously stirred. 3.6 parts of cyanuric chloride was added thereto and stirred for 30 minutes at 0 to 5° C. to obtain a suspension liquid. Subsequently, 100 parts of the wet cake of the compound represented by the above formula (100) was dissolved in 200 parts of water to obtain a solution, to which the above suspension liquid was added dropwise over 30 minutes. After the completion of the dropwise addition, it was stirred for 6 hours under the conditions of pH 6 to 8 and 25 to 45° C. To the resulting liquid, 0.9 parts of piperazine was added, and stirred for 2 hours under the conditions of pH 7 to 9 and 75 to 90° C. After cooling the resulting reaction liquid to 20 to 25° C., 2000 parts of 2-propanol was added to this reaction liquid, and stirred for 2 hours at 20 to 25° C. The resulting precipitated solid was filtered and separated to obtain 92.1 parts of a wet cake. By drying this wet cake with an 80° C. hot-air dryer, 12.0 parts of a sodium salt of a compound according to the present invention represented by the following formula (200) (λmax: 418.5 nm) was obtained.

[Preparation of Ink]

An ink of Example 18 was prepared as in Example 1 except that the compound represented by the above formula (200) was used instead of the compound represented by the above formula (101).

[Ink-Jet Recording]

Ink-jet recording was performed with an ink-jet printer (Canon, Inc., Product name: PIXUS ip7230) to allow each of the inks from Example 18 and Comparative Examples 1, 2 above to be attached on the following glossy papers 1 to 4. Upon performing recording, image patterns were created so that the density can be obtained in a gradation of 6 levels: 100%, 85%, 70%, 55%, 40%, and 25% to obtain a half-tone recorded article. The resulting recorded article was used as a test piece to perform the following tests.

Glossy paper 1: Canon, Inc., Product name: Canon Photograph paper, platinum grade (PT-201)

Glossy paper 2: Seiko Epson Corporation, Product name: Photograph paper Crispia

Glossy paper 3: Brother Industries, Ltd., Product name: BP71G

Glossy paper 4: FUJIFILM Corporation, Product name: Gasai Photo-finishing Pro

[Color Measurements of Recorded Image]

When required, color measurements of a recorded image were performed using a colorimeter (Product name SpectroEye from X-rite, Inc.). Color measurements were performed under the conditions of a density standard of DIN NB, a wide viewing angle of 2 degrees, a light source of D65.

[Xenon Light Resistance Tests]

A test piece with a holder was placed in a xenon weatherometer XL75 (Suga Test Instruments Co., Ltd.), and irradiated for 168 hours at a temperature of 24° C., a humidity of 60% RH, and an illuminance of 100 klux. A gradation portion with a density of 70% of each test piece was subjected to color measurements of reflection densities before and after the test. A coloring matter persistence rate was computed from the reflection densities obtained, and evaluation was performed using the following 4-grade criteria. A larger numerical value indicates a superior coloring matter persistence rate. Evaluation results are shown in Table 58 below.

(Evaluation Criteria of Light Resistance)

A coloring matter persistence rate of 90% or more: A

A coloring matter persistence rate of 85% or more and less than 90%: B

A coloring matter persistence rate of 81% or more and less than 85%: C

A coloring matter persistence rate of less than 81%: D

(Formula for Computing Coloring Matter Persistence Rate) Coloring matter persistence rate (%)=(reflection density after test/reflection density before test)×100

TABLE 58 Results from light

resistance tests 1 2 3 4 Example 18 A A A A Comparative  1 C B D B Example  2 C D D D

As clearly seen in Table 58, Examples 18 showed better results than Comparative Examples 1, 2 for each glossy paper in the light resistance tests. 

The invention claimed is:
 1. A compound represented by the following formula (1) or (2) or a salt thereof:

wherein, each Q independently represents a halogen atom, each R¹¹ and R¹² independently represents an alkyl group substituted with an ionic hydrophilic group, and A¹ is a group represented by the following formula (A 1-1), a group represented by the following formula (A1-2), a C1-C3 alkoxy-substituted alkylamino group, a C2-C6 alkyl-monosubstituted amino group having two or more hydroxy groups, a group represented by the following formula (A1-3), a group represented by the following formula (A1-4), or a cyclic amine group,

wherein, R^(A11) represents a branched alkylene group, and the symbol “*” represents a position of attachment to a triazine ring,

wherein, n represents an integer of 1 to 6, and the symbol “*” represents a position of attachment to the triazine ring,

wherein, m represents an integer of 1 to 6, n represents an integer of 1 to 5, and the symbol “*” represents a position of attachment to the triazine ring,

wherein, n represents an integer of 2 to 6, and the symbol “*” represents a position of attachment to the triazine ring,

wherein, each Q²¹ to Q²⁴ independently represents a halogen atom, and each R²¹ to R²⁴ independently represents an alkyl group substituted with an ionic hydrophilic group, and A² represents a divalent group, wherein the compound represented by the formula (1) is represented by any of the following formulae (1-11) to (1-15):


2. An ink comprising the compound or a salt thereof according to claim
 1. 3. The ink according to claim 2, further comprising a water-soluble organic solvent.
 4. An ink-jet recording method, comprising discharging a droplet of the ink according to claim 2 in response to a recording signal to allow for attachment to a recording medium.
 5. The inkjet recording method according to claim 4, wherein the recording medium is plain paper or a sheet having an ink receiving layer.
 6. A recording medium to which the compound or a salt thereof according to claim 1 is attached.
 7. An ink-jet printer loaded with a container containing the ink according to claim
 2. 8. An ink-jet printer loaded with a container containing the ink according to claim
 3. 